Liquid crystal compound, liquid crystal composition and liquid crystal display device

ABSTRACT

The invention provides a liquid crystal compound having stability to heat, light and so forth, a wide temperature range of a nematic phase, a small viscosity, a suitable optical anisotropy, a suitable elastic constant K 33 , a suitable and negative dielectric anisotropy, and an excellent compatibility with other liquid crystal compounds. The invention provides a liquid crystal composition containing the compound described above and having stability to heat, light and so forth, a small viscosity, a suitable optical anisotropy, a suitable and negative dielectric anisotropy, a suitable elastic constant K 33 , a low threshold voltage, a high maximum temperature of a nematic phase, and a low minimum temperature of the nematic phase. 
     The invention also provides a liquid crystal display device having a short response time, a small power consumption, a low driving voltage, and a large contrast, and containing the composition described above which can be used in a large temperature range. 
     For example, a liquid crystal compound having four or more rings in which the central ring has 2,3-difluorophenoxy such as trans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl)phenoxymethyl]-trans-4-pentylbicyclohexyl is provided. Further provided is a liquid crystal composition containing the compound, and a liquid crystal display device using this liquid crystal composition.

FIELD OF THE INVENTION

The invention relates to a new liquid crystal compound which is usefulas a material for a liquid crystal display device, and a liquid crystalcomposition including this compound. The invention relates morespecifically to a compound which has four or more rings and the centralring among these being 2,3-difluorophenoxy, a liquid crystal compositionincluding this compound, and a liquid crystal display device includingthis liquid crystal composition.

BACKGROUND OF THE INVENTION

A liquid crystal display device typified by a liquid crystal displaypanel, a liquid crystal display module and so forth utilizes opticalanisotropy, dielectric anisotropy and so forth which are possessed by aliquid crystal compound (a liquid crystal compound means in thisinvention a generic term for a compound having a nematic phase, asmectic phase and so forth, and a compound having no liquid crystalphases but useful as a component of a liquid crystal composition.). Asoperation modes of this liquid crystal display device, a variety ofmodes are known, such as a PC (phase change), TN (twisted nematic), STN(super twisted nematic), BTN (bistable twisted nematic), ECB(electrically controlled birefringence), OCB (optically compensatedbend), IPS (inch-plane switching), VA (vertical alignment), or PSA(Polymer sustained alignment) mode.

It is known that among these operation modes, the ECB, IPS, VA modes andso forth are utilizing a homeotropic property of liquid crystalmolecules, and that a limited-viewing angle which is a disadvantage ofconventional display modes such as the TN and STN modes can be improvedespecially by use of the IPS and VA modes.

A large number of liquid crystal compounds in which hydrogen at thelateral position on the benzene-ring is replaced by fluorine have beenstudied until now as components for a liquid crystal composition havinga negative dielectric anisotropy which is usable to the liquid crystaldisplay device with these operation modes (For example, refer to thepatent documents Nos. 1 to 5 or the non-patent documents Nos. 1 and 2.).

For example, the patent document No. 1 or the non-patent document No. 1shows a three-ring compound such as formula (ref. 1) or formula (ref.2). This compound has a range exhibiting liquid crystal phases (amesophase range) that is narrow, and a clearing point that is low whenused for a liquid crystal composition.

The patent document No. 2 shows a four-ring compound such as formula(ref. 3). However, the dielectric anisotropy of this compound is notsufficiently large negatively.

The patent document No. 3 shows a four-ring compound such as formula(ref. 4) or formula (ref. 5). However, a clearing point is low when thiscompound is used for a liquid crystal composition.

The patent document No. 4 shows a four-ring compound such as formula(ref. 6). However, the dielectric anisotropy of this compound is notsufficiently large negatively.

The patent document No. 5 shows a four-ring compound such as formula(ref. 7). However, the dielectric anisotropy of this compound is notsufficient large negatively.

The non-patent document No. 2 shows a four-ring compound such as formula(ref. 8). However, this compound has a range exhibiting liquid crystalphases (a mesophase range) that is narrow, and a clearing point that islow when used for a liquid crystal composition. Furthermore, thedielectric anisotropy has a positive value instead of a negative one.

The patent documents cited herein are No. 1: German Patent 3,906,058 C;No. 2: WO 89/08687 A; No. 3: WO 89/08689 A; No. 4: JP 2002-193853 A; andNo. 5: German Patent 10,136,751 A (2002). The non-patent documents citedare No. 1: Liquid Crystals (1994), 16 (4), 625-641 and No. 2: LiquidCrystals (2004), 31 (8), 1151-1158.

DISCLOSURE OF THE INVENTION Subjects to be Solved by the Invention

In view of the circumstances described above, even liquid crystaldisplay devices by means of operation modes such as the IPS and VA modesare more problematic than CRTs for use of display devices, and, forexample, an improvement of a response speed, an improvement of contrast,and a decrease in driving voltage are required.

The display devices operated by means of the IPS or VA mode describedabove are composed of a liquid crystal composition mainly having anegative dielectric anisotropy. In order to further improve thesecharacteristics and so forth, it is required for the liquid crystalcompounds contained in this liquid crystal composition to have thecharacteristics shown in items (1) to (8) below. That is to say:

(1) being chemically stable and physically stable,(2) having a high clearing point (transition temperature on a liquidcrystal phase-an isotropic phase),(3) being low in a minimum temperature of liquid crystal phases (anematic phase, a smectic phase and so forth), especially that of thenematic phase,(4) being low in viscosity,(5) having a suitable optical anisotropy,(6) having a suitable and negative dielectric anisotropy,(7) having a suitable elastic constant K₃₃ (K₃₃: bend elastic constant),and(8) being excellent in compatibility with other liquid crystalcompounds.

A voltage holding ratio can be increased by use of a compositioncontaining a chemically and physically stable liquid crystal compound asdescribed in item (1), for a display device.

The temperature range of a nematic phase can be widened in a compositionwhich contains a liquid crystal compound having a high clearing point ora low minimum temperature of liquid crystal phases as described in items(2) and (3), and thus a display device is usable in a wide temperaturerange.

Furthermore, when a composition containing a compound with a smallviscosity as described in item (4) or a compound having a large elasticconstant K₃₃ with regard to in item (7) is used for a display device,response speed can be improved, and in the case of a display deviceusing a composition which contains a compound having a suitable opticalanisotropy as described in item (5), an improvement of the contrast in adisplay device can be expected. Optical anisotropy is required in arange of small to large values according to designs of a device.Recently, a method for improving the response speed by means of asmaller cell thickness has been investigated, whereby a liquid crystalcomposition having a suitable optical anisotropy has also been required.

Moreover, when a liquid crystal compound has a large negative dielectricanisotropy, the threshold voltage of the liquid crystal compositioncontaining this compound can be decreased. Hence, the driving voltage ofa display device can be decreased and electric power consumption canalso be decreased in the case of a display device using a compositioncontaining a compound which has a suitable and negative dielectricanisotropy as described in item (6). Further, the driving voltage of adisplay device can be decreased and the electric power consumption canalso decreased by use of a composition containing a compound with asmall elastic constant K₃₃ with regard to item (7).

The liquid crystal compound is generally used as a composition preparedby being mixed with many other liquid crystal compounds in order toexhibit characteristics which cannot be attained with a single compound.Accordingly, it is desirable that a liquid crystal compound used for adisplay device has an excellent compatibility with other liquid crystalcompounds and so forth, as described in item (8). Because the displaydevice may also be used in a wide temperature range including a lowertemperature than the freezing point, a compound which exhibits anexcellent compatibility even in a low temperature region may bedesirable.

The first aim of the invention is to provide a liquid crystal compoundhaving stability to heat, light and so forth, a nematic phase in a widetemperature range, a small viscosity, a suitable optical anisotropy, anda suitable elastic constant K₃₃, and further having a suitable andnegative dielectric anisotropy and an excellent compatibility with otherliquid crystal compounds.

The second aim of the invention is to provide a liquid crystalcomposition which satisfies at least one characteristic among thecharacteristics such as stability to heat, light and so forth, a smallviscosity, a suitable optical anisotropy, a suitable elastic constantK₃₃, and a low threshold voltage, and also a high maximum temperature ofa nematic phase (phase-transition temperature on a nematic phase-anisotropic phase) and a low minimum temperature of the nematic phase. Itis also the aim to provide a liquid crystal composition having asuitable balance with respect to at least two characteristics.

The third aim of the invention is to provide a liquid crystal displaydevice, which includes the composition described above, having a shortresponse time, a small power consumption, a low driving voltage, a largecontrast, and a wide and usable temperature range.

Means to Solve the Subjects

The inventors have keenly studied in view of these subjects describedabove and thus found that a compound which has four or more rings andthe central ring among these being 2,3-difluorophenoxy has at least onecharacteristic among characteristics such as stability to heat, lightand so forth, liquid crystal phases in a wide temperature range, a smallviscosity, a suitable optical anisotropy, a suitable elastic constantK₃₃, a large negative dielectric anisotropy, and an excellentcompatibility with other liquid crystal compounds.

They have also found that a liquid crystal composition including thiscompound has at least one characteristic among characteristics such as alow threshold voltage, a high maximum temperature of a nematic phase,and a low minimum temperature of the nematic phase in addition to thecharacteristics above, or has at least two of the characteristics aresuitably balanced.

They have further found that a liquid crystal display device includingthis composition has a short response time, a small electric powerconsumption, a small driving voltage, a large contrast ratio, and a wideand usable temperature range. On the basis of the above findings, theinvention has been completed.

The invention includes item 1 to item 17 described below.

[Item 1] A compound represented by formula (a):

in formula (a),

Ra and Rb are each independently hydrogen, alkyl having 1 to 12 carbons,alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons,alkoxyalkyl having 2 to 11 carbons, or alkenyloxy having 2 to 11carbons, and in these alkyl, alkenyl, alkoxy, alkoxyalkyl, oralkenyloxy, arbitrary hydrogen may be replaced by fluorine;

ring A¹, ring A², ring A³, and ring A⁴ are each independently1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl,pyrimidine-2,5-diyl, pyridine-2,5-diyl, 1,4-phenylene,naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or1,2,3,4-tetrahydronaphthalene-2,6-diyl, and in these rings, arbitraryhydrogen may be replaced by fluorine;

Z¹ and Z² are each independently a single bond, —(CH₂)₂—, —(CH₂)₄—,—CH═CH—, —C≡C—, —CH₂O—, —OCH₂—, —COO—, —OCO—, —CF₂O—, or —OCF₂—;

W is —CH₂—, —CO—, or —CF₂—; and

m and n are each independently 0, 1, or 2, and the sum of m and n is 1or 2.

[Item 2] The compound according to item 1, wherein in formula (a),

Ra and Rb are each independently alkyl having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkoxy having 1 to 11 carbons, alkoxyalkylhaving 2 to 11 carbons, or alkenyloxy having 2 to 11 carbons; and

ring A¹, ring A², ring A³, and ring A⁴ are each independently1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl,pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene,3-fluoro-1,4-phenylene, or 2,3-difluoro-1,4-phenylene.

[Item 3] A compound represented by any one of formula (a-1) and formula(a-2):

in formula (a-1) and formula (a-2),

Ra¹ and Rb¹ are each independently alkyl having 1 to 12 carbons, alkoxyhaving 1 to 11 carbons, or alkenyl having 2 to 12 carbons;

ring A⁵, ring A⁶, ring A⁷, and ring A⁸ are each independently1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or3-fluoro-1,4-phenylene;

Z³ and Z⁴ are each independently a single bond, —(CH₂)₂—, —CH═CH—,—C≡C—, —CH₂O—, —OCH₂—, —COO—, or —OCO—; and

W is —CH₂—, —CO—, or —CF₂—.

[Item 4] The compound according to item 3, wherein in formulas (a-1) and(a-2), Z³ and Z⁴ are each independently a single bond or —(CH₂)₂—.[Item 5] A compound represented by any one of formulas (a-1-1) to(a-1-6) and formulas (a-2-1) to (a-2-6):

in formulas (a-1-1) to (a-1-6) and formulas (a-2-1) to (a-2-6), Ra¹ andRb¹ are each independently alkyl having 1 to 12 carbons, alkoxy having 1to 11 carbons, or alkenyl having 2 to 12 carbons; and W is —CH₂—, —CO—,or —CF₂—.

[Item 6] The compound according to item 5, wherein W is —CH₂— informulas (a-1-1) to (a-1-6) and formulas (a-2-1) to (a-2-6).[Item 7] The compound according to item 5, wherein W is -CO— in formulas(a-1-1) to (a-1-6) and formulas (a-2-1) to (a-2-6).[Item 8] The compound according to item 5, wherein W is —CF₂— informulas (a-1-1) to (a-1-6) and formulas (a-2-1) to (a-2-6).[Item 9] A liquid crystal composition having a negative dielectricanisotropy that includes a first component which is at least onecompound selected from the compounds according to any one of items 1 to8 and a second component which is at least one compound selected fromthe group of compounds represented by formulas (e-1) to (e-3):

in formulas (e-1) to (e-3),

Ra₁₁ and Rb₁₁ are each independently alkyl having 1 to 10 carbons, andin this alkyl, —CH₂— may be nonadjacently replaced by —O—, —(CH₂)₂— maybe nonadjacently replaced by —CH=CH—, and hydrogen may be replaced byfluorine;

ring A¹¹, ring A¹², ring A¹³, and ring A¹⁴ are each independently1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,3-fluoro-1,4-phenylene,pyrimidine-2,5-diyl, 1,3-dioxane 2,5-diyl, ortetrahydropyran-2,5-diyl; and

Z¹¹, Z¹², and Z¹³ are each independently a single bond, —(CH₂)₂—,—CH═CH—, —C≡C—, —COO—, or —CH₂O—.

[Item 10] A liquid crystal composition having a negative dielectricanisotropy that includes a first component which is at least onecompound selected from the group of compounds represented by formulas(a-1-1) to (a-1-6) and formulas (a-2-1) to (a-2-6) according to item 5,and a second component selected from the group of compounds representedby formulas (e-1) to (e-3) according to item 9.[Item 11] The liquid crystal composition according to item 10, whereinthe content ratio of the first component is in the range of 5% to 60% byweight, and the content ratio of the second component is in the range of40% to 95% by weight, based on the total weight of the liquid crystalcomposition.[Item 12] The liquid crystal composition according to item 9 or 10, thatfurther includes a third component which is at least one compoundselected from the group of compounds represented by formulas (g-1) to(g-6), in addition to the first and second components:

in formulas (g-1) to (g-6),

Ra₂₁ and Rb₂₁ are each independently hydrogen or alkyl having 1 to 10carbons, and in this alkyl, —CH₂— may be nonadjacently replaced by —O—,—(CH₂)₂— may be nonadjacently replaced by —CH═CH—, and hydrogen may bereplaced by fluorine;

ring A²¹, ring A²², and ring A²³ are each independently1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,3-fluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, ortetrahydropyran-2,5-diyl;

Z²¹, Z²², and Z²³ are each independently a single bond, —(CH₂)₂—,—CH═CH—, —C≡C—, —OCF₂—, —CF₂O—, —OCF₂CH₂CH₂—, —CH₂CH₂CF₂O—, —COO—,—OCO—, —OCH₂—, or —CH₂O—;

Y¹, Y², Y³, and Y⁴ are each independently fluorine or chlorine;

q, r, and s are each independently 0, 1, or 2, and q+r+s is 1, 2, or 3;and

t is 0, 1, or 2.

[Item 13] The liquid crystal composition according to item 12, whereinthe third component is at least one compound selected from the group ofcompounds represented by formulas (h-1) to (h-7):

in formulas (h-1) to (h-7),

Ra₂₂ and Rb₂₂ are a straight-chain alkyl having 1 to 8 carbons, astraight-chain alkenyl having 2 to 8 carbons, or alkoxy having 1 to 7carbons;

Z²⁴, Z²⁵, and Z²⁶ are a single bond, —(CH₂)₂—, —COO—, —OCO—, —CH₂O—, or—OCH₂—; and

Y¹ and Y² are simultaneously fluorine or one of Y¹ and Y² is fluorineand the other is chlorine.

[Item 14] A liquid crystal composition having a negative dielectricanisotropy that includes a first component which is at least onecompound selected from the group of compounds represented by formulas(a-1-1) to (a-1-6) and formulas (a-2-1) to (a-2-6) according to item 5,a second component which is at least one compound selected from thegroup of compounds represented by formulas (e-1) to (e-3) according toitem 9, and a third component which is at least one compound selectedfrom the group of compounds represented by formulas (h-1) to (h-7)according to item 13.[Item 15] The liquid crystal composition according to any one of items12 to 14, wherein the content ratio of the first component is in therange of 5% to 60% by weight, the content ratio of the second componentis in the range of 20% to 75% by weight, and the content ratio of thethird component is in the range of 20% to 75% by weight, based on thetotal weight of the liquid crystal composition.[Item 16] A liquid crystal display device that includes the liquidcrystal composition according to any one of items 9 to 15.[Item 17] The liquid crystal display device according to item 16,wherein the operation mode thereof is a VA mode or an IPS mode, and thedriving mode thereof is an active matrix mode.

EFFECT OF THE INVENTION

The liquid crystal compound of the invention has stability to heat,light and so forth, liquid crystal phases in a wide temperature range, asmall viscosity, a suitable optical anisotropy, and a suitable elasticconstant K₃₃ (K₃₃: bend elastic constant), and also has a suitable andnegative dielectric anisotropy and an excellent compatibility with otherliquid crystal compounds. The liquid crystal compound is excellentespecially in view of a large negative dielectric anisotropy, a highmaximum temperature of a nematic phase, and then an excellentcompatibility with other liquid crystal compounds.

The liquid crystal composition of the invention has a small viscosity, asuitable optical anisotropy, a suitable elastic constant K₃₃, a suitableand negative dielectric anisotropy, a low threshold voltage, a highmaximum temperature of a nematic phase, and a low minimum temperature ofthe nematic phase. The liquid crystal composition is excellentespecially in view of a suitable and negative optical anisotropy and ahigh maximum temperature of a nematic phase.

The liquid crystal display device of the invention is characterized byincluding the above composition, and consequently has a short responsetime, a small power consumption, a small driving voltage, a largecontrast ratio, and a wide and usable temperature range. The abovecomposition can be suitably used for a liquid crystal display devicewith the display mode such as a PC, TN, STN, ECB, OCB, IPS, VA, or PSAmode. It can be suitably used especially for a liquid crystal displaydevice with the IPS, VA, or PSA mode.

BEST EMBODIMENT TO CARRY OUT THE INVENTION

Terms are used in this specification as follows. A liquid crystalcompound is a generic term for a compound having liquid crystal phasessuch as a nematic phase and a smectic phase, and also for a compoundhaving no liquid crystal phases but useful as a component for a liquidcrystal composition. The terms, a liquid crystal compound, a liquidcrystal composition, and a liquid crystal display device may beabbreviated to a compound, a composition, and a device, respectively. Aliquid crystal display device is a generic term for a liquid crystaldisplay panel and a liquid crystal display module. A maximum temperatureof a nematic phase is the phase transition temperature of the nematicphase to an isotropic phase, and may simply be abbreviated to a maximumtemperature. A minimum temperature of the nematic phase may simply beabbreviated to a minimum temperature. The compounds represented byformula (a) may be abbreviated to the compound (a). In formula (a) andso forth, the symbols A¹, A², A³, A⁴ and so forth surrounded by ahexagonal shape correspond to ring A¹, ring A², ring A³, ring A⁴ and soforth, respectively. The amount of a compound expressed as a percentagemeans a weight percentage (% by weight) based on the total weight of itscomposition. The invention will be further explained below.

[Liquid Crystal Compound (a)]

The liquid crystal compound of the invention has a structure representedby formula (a) (hereinafter the compound is also referred to as “thecompound (a)”).

In formula (a) , Ra and Rb are each independently hydrogen, alkyl having1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11carbons, alkoxyalkyl having 2 to 11 carbons, or alkenyloxy having 2 to11 carbons, and in these alkyl, alkenyl, alkoxy, alkoxyalkyl, andalkenyloxy, hydrogen may be replaced by fluorine.

Ring A¹, ring A², ring A³, and ring A⁴ are each independently1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl,pyrimidine-2,5-diyl, pyridine-2,5-diyl, 1,4-phenylene,naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or1,2,3,4-tetrahydronaphthalene-2,6-diyl and in these rings, hydrogen maybe replaced by fluorine.

When m is 2, two rings A¹ may be the same or different, and when n is 2,two rings A⁴ may be the same or different.

The symbols Z¹ and Z² are each independently a single bond, —(CH₂)₂—,—(CH₂)₄—, —CH═CH—, —C≡C—, —CH₂O—, —OCH₂—, —COO—, —OCO—, —CF₂O—, or—OCF₂—.

When m is 2, two rings Z¹ may be the same or different, and when n is 2,two rings Z² may be the same or different.

The symbol W is —CH₂—, —CO—, or —CF₂—.

The symbols m and n are each independently 0, 1, or 2, and the sum of mand n is 1 or 2.

As described above, the compound (a) has four or more rings, the centralring of these is 2,3-difluorophenoxy, and the 2,3-difluorophenoxy isbonded to another ring through a single bond at the 4-position. Thecompound (a) has liquid crystal phases in a wide temperature range, asmall viscosity, a suitable optical anisotropy, a large negativedielectric anisotropy, and an excellent compatibility with other liquidcrystal compounds by an effect of the structure. The compound (a) isexcellent especially in view of excellent compatibility with otherliquid crystal compounds in spite of a large negative dielectricanisotropy and a high maximum temperature of a nematic phase.

It is possible to adjust optionally physical properties, such as opticalanisotropy and dielectric anisotropy by suitably selecting Ra, Rb, ringA¹, ring A², ring A³, ring A⁴, Z¹, Z², W, m, and n of the compound (a).Desirable Ra, Rb, ring A¹, ring A², ring A³, ring A⁴, Z¹, Z², W, m, andn of the compound (a) and the effects of these kinds on the physicalproperties of the compound (a) will be explained below.

In formula (a), Ra and Rb are each independently hydrogen, alkyl having1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11carbons, alkoxyalkyl having 2 to 11 carbons, or alkenyloxy having 2 to11 carbons and in these alkyl, alkenyl, alkoxy, alkoxyalkyl, andalkenyloxy, arbitrary hydrogen may be replaced by fluorine.

Specific examples of the alkyl include —CH₃, —C₂H₅, —C₃H₇, —C₄H₉,—C₅H₁₁, —C₆H₁₃, —C₇H₁₅, —C₈H₁₇, —C₉H₁₉, —C₁₀H₂₁, —C₁₁H₂₃, and —C₁₂H₂₅;

specific examples of the alkenyl include —CH═CH₂, —CH═CHCH₃, —CH₂CH═CH₂,—CH═CHC₂H₅, —CH₂CH═CHCH₃, —(CH₂)₂CH═CH₂, —CH═CHC₃H₇, —CH₂CH═CHC₂H₅,—(CH₂)₂CH═CHCH₃, and —(CH₂)₃CH═CH₂;

specific examples of the alkoxy include —OCH₃, —OC₂H₅, —OC₃H₇, —OC₄H₉,—OC₅H₁₁, —OC₆H₁₃, —OC₇H₁₅, —OC₈H₁₇, —OC₉H₁₉, —OC₁₀H₂₁, and —OC₁₁H₂₃;

specific examples of the alkoxyalkyl include —CH₂OCH₃, —CH₂OC₂H₅,—CH₂OC₃H₇, —(CH₂)₂OCH₃, —(CH₂)₂OC₂H₅, —(CH₂)₂OC₃H₇, —(CH₂)₃OCH₃,—(CH₂)₄OCH₃, and —(CH₂)₅OCH₃; and

specific examples of the alkenyloxy include —OCH₂CH═CH₂, —OCH₂CH═CHCH₃,and —OCH₂CH═CHC₂H₅.

Specific examples of the alkyl in which hydrogen is replaced by halogeninclude —CH₂F, —CHF₂, —CF₃, —(CH₂)₂F, —CF₂CH₂F, —CF₂CHF₂, —CH₂CF₃,—CF₂CF₃, —(CH₂)₃F, —(CF₂)₂CF₃, —CF₂CHFCF₃, and —CHFCF₂CF₃;

specific examples of the alkenyl in which hydrogen is replaced byhalogen include —CH═CHF, —CH═CF₂, —CF═CHF, —CH═CHCH₂F, —CH═CHCF₃, and—(CH₂)₂CH═CF₂; and

specific examples of the alkoxy in which hydrogen is replaced by halogeninclude —OCF₃, —OCHF₂, —OCH₂F, —OCF₂CF₃, —OCF₂CHF₂, —OCF₂CH₂F,—OCF₂CF₂CF₃, —OCF₂CHFCF₃, and —OCHFCF₂CF₃.

When Ra and Rb are straight-chains in the compound (a), the temperaturerange of liquid crystal phases is wide and viscosity is small. Thecompound in which Ra or Rb is an optically active group is useful as achiral dopant . A reverse twist domain which will occur in a device canbe prevented by adding this compound to a composition. The compound inwhich Ra and Rb are optically inactive groups is useful as a componentof a composition.

When Ra or Rb is alkenyl, a desirable configuration depends on theposition of a double bond. A desirable configuration of —CH═CH— in thealkenyl depends on the position of the double bond. Atrans-configuration is preferable in the alkenyl having a double bond atan odd-numbered position, such as —CH═CHCH₃, —CH═CHC₃H₇,—(CH₂)₂CH═CHCH₃, and —(CH₂)₄CH═CHC₃H₇. A cis-configuration is preferablein the alkenyl having a double bond at an even-numbered position, suchas —CH₂CH═CHCH₃, —(CH₂)₃CH═CHC₂H₅, and —(CH₂)₅CH═CHCH₃. An alkenylcompound having a desirable configuration has a high maximum temperatureor a wide temperature range of liquid crystal phases and a large elasticconstant ratio K₃₃/K₁₁ (K₃₃: bend elastic constant, K₁₁: spray elasticconstant).

In the alkenyl, CH₂═CH—CH₂—CH₂—CH═CH— in which the double bonds arenonadjacent is preferable to CH₂═CH—CH═CH—CH₂—CH₂—in which the doublebonds are adjacent, in view of the stability of the compound.

Examples of desirable Ra and Rb are —CH₃ , —C₂H₅,—C₃H₇, —C₄H₉,—C₅H₁₁,—C₆H₁₃, —C₇H₁₅, —CH═CH₂, —CH═CHCH₃, —CH₂CH═CH₂, —CH═CHC₂ H₅,—CH₂CH═CHCH₃, —(CH₂)₂CH═CH₂, —CH═CHC₃H₇, —CH₂CH═CHC₂H₅, —(CH₂)₂CH═CHCH₃,—(CH₂)₃CH═CH₂, —OCH₃, —OC₂H₅, —OC₃H₇, —OC₄H₉, —OC₅H₁₁, —OC₆H₁₃,—CH₂OCH₃, —CH₂OC₂H₅, —CH₂OC₃H₇, —(CH₂)₂OCH₃, —(CH₂)₂OC₂H₅, —OCH₂ CH═CH₂,—OCH₂CH═CHCH₃, —OC₂H₄CH═CH₂, —OC₂H₄CH═CHCH₃, —OC₃H₆CH═CH₂, and—OC₃H₆CH═CHCH₃.

Examples of more desirable Ra and Rb are —CH₃, —C₂H₅, —C₃H₇, —C₄H₉,—C₅H₁₁, —CH═CH₂, —CH═CHCH₃, —(CH₂)₂CH═CH₂, —CH═CHC₃H₇, —(CH₂)₂CH═CHCH₃,—OCH₃, —OC₂H₅, —OC₃H₇, —OC₄H₉, —CH₂OCH₃, —CH₂OC₂H₅, —CH₂OC₃H₇,—OCH₂CH═CH₂, —OCH₂CH═CHCH₃, and —OC₃H₆CH═CHCH₃.

Examples of most desirable Ra and Rb are —CH₃, —C₂H₅, —C₃H₇, —C₄H₉,—C₅H₁₁, —CH═CH₂, —CH═CHCH₃, —(CH₂)₂CH═CH₂, —CH═CHC₃H₇, —(CH₂)₂CH═CHCH₃ ,—OCH₃, —OC₂H₅, —OC₃H₇, and —OC₄H₉.

In formula (a) , ring A¹, ring A², ring A³, and ring A⁴ are eachindependently 1,4-cyclohexylene, 1,4-cyclohexenylene,tetrahydropyran-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl,1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or1,2,3,4-tetrahydronaphthalene-2,6-diyl and in these rings, hydrogen maybe replaced by fluorine.

Specific examples of ring A¹, ring A², ring A³, and ring A⁴ includerings (R-1) to (R-36).

There are trans-isomer and cis-isomer as a stereoisomer in rings (R-1)to (R-3) and rings (R-30) to (R-36), and the trans-isomer is preferablein view of a higher maximum temperature.

When any one or all of ring A¹, ring A², ring A³, and ring A⁴ are1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, ornaphthalene-2,6-diyl, wherein arbitrary hydrogen may be replaced byhalogen, the optical anisotropy is large. When any one or all of ringA¹, ring A², ring A³, and ring A⁴ are 1,4-cyclohexylene,1,4-cyclohexenylene, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, theoptical anisotropy is small.

When at least two rings are 1,4-cyclohexylene, the maximum temperatureis high, the optical anisotropy is small, and the viscosity is small.When at least one ring is 1,4-phenylene, the optical anisotropy iscomparatively large and the orientational order parameter is large. Whenat least two rings are 1,4-phenylene, the optical anisotropy is large,the temperature range of liquid crystal phases is wide, and the maximumtemperature is high.

When any one or all of ring A¹, ring A², ring A³, and ring A⁴ are rings(R-7) to (R-9), rings (R-27) to (R-29), ring (R-32), or ring (R-35), thedielectric anisotropy is large and negative.

When any one or all of ring A¹, ring A², ring A³, and ring A⁴ are rings(R-1) to (R-3), rings (R-6) to (R-12), or rings (R-30) to (R-36), thestability of the compound is high.

When ring A¹, ring A², ring A³, and ring A⁴ are ring (R-1) or rings(R-6) to (R-9), the compounds are desirable, because the stability ishigh, the temperature range of liquid crystal phases is wide and themaximum temperature of a nematic phase is high.

When ring A^(1,) ring A², ring A³, and ring A⁴ are rings (R-1) to (R-8), the viscosity is small.

When ring A¹, ring A², ring A³, and ring A⁴ are ring (R-1) or rings(R-6) to (R-8), the compounds are desirable, because the stability ishigh, the temperature range of the liquid crystal phases is wide, theviscosity is small, and the maximum temperature of a nematic phase ishigh.

In formula (a), Z¹ and Z² are each independently a single bond,—(CH₂)₂—, —(CH₂)₄—, —CH═CH—, —C≡C—, —CH₂O—, —OCH₂—, —COO—, —OCO—,—CF₂O—, or —OCF₂—.

Desirable Z¹ and Z² are a single bond and —(CH2)₂—, and more desirableZ¹ and Z² are a single bond.

When any one or all of Z¹, Z², and Z³ are a single bond or —(CH₂)₂—,heat resistance or light resistance is excellent. When any one or all ofthe bonding groups are —CH═CH—, the temperature range of liquid crystalphases is wide and the elastic constant ratio K₃₃/K₁₁ (K₃₃: bend elasticconstant, K₁₁: spray elastic constant) is large. When any one or all ofthe bonding groups are —CH═CH— or —C≡C—, the optical anisotropy islarge.

A trans isomer is preferable in the configuration of a double bond suchas —CH═CH—, because the range of a mesophase is wide and the maximumtemperature is high.

In formula (a), W is —CH₂—, —CO—, or —CF₂—. When W is —CH₂—, —CO—, or—CF₂—, the temperature range of liquid crystal phases is wide,dielectric anisotropy is large and negative, the stability is high,compatibility with other liquid crystal compounds is excellent, and acomposition which include the compound has a high maximum temperature ofa nematic phase. In particular, when W is —CH₂—, the compound isdesirable, because its stability is high, its dielectric anisotropy islarge and negative, and a composition which include the compound has ahigh maximum temperature of a nematic phase. When W is —CO—, thecompound is desirable, because its temperature range of liquid crystalphases is wide, its compatibility with other liquid crystal compounds isexcellent, and a composition which include the compound has a highmaximum temperature of a nematic phase. When W is —CF₂—, the compound isdesirable, because its compatibility with other liquid crystal compoundsis excellent.

In formula (a), m and n are each independently 0, 1, or 2, and the sumof m and n is 1 or 2. When the sum of m and n is 1, a composition whichincludes the compound has a high maximum temperature of a nematic phase,and when the sum of m and n is 2, a composition which includes thecompound has a higher maximum temperature of the nematic phase.

When liquid crystal compounds have the structure represented by formula(a), they have a large negative dielectric anisotropy, wide liquidcrystal phases, and an excellent compatibility with other liquid crystalcompounds. Furthermore, they have stability to heat, light and so forth,a nematic phase in a wide temperature range, a small viscosity, asuitable optical anisotropy, and a suitable elastic constant K₃₃. Theliquid crystal composition including this liquid crystal compound (a) isstable under conditions in which a liquid crystal display device isusually used, and this compound does not deposit its crystals (or itssmectic phase) even when the composition is kept at a low temperature.

A desirable example of the compound (a) is the compound represented byany one of formulas (a-1) and (a-2). The compound is stable chemicallyand has liquid crystal phases in a wide temperature range, a smallviscosity, a suitable optical anisotropy, a large negative dielectricanisotropy, a suitable elastic constant K₃₃, and an excellentcompatibility with other liquid crystal compounds by the effect of sucha structure. Moreover, a composition which includes the compound has ahigh maximum temperature of a nematic phase. The composition isexcellent especially in view of chemical stability, liquid crystalphases in a wide temperature range, and an excellent compatibility withother liquid crystal compounds.

In formulas (a-1) and (a-2), Ra¹ and Rb¹ are each independently alkylhaving 1 to 12 carbons, alkoxy having 1 to 11 carbons, or alkenyl having2 to 12 carbons;

ring A⁵, ring A⁶, ring A⁷, and ring A⁸ are each independently1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or3-fluoro-1,4-phenylene;

Z³ and Z⁴ are each independently a single bond, —(CH₂)₂—, —CH═CH—,—C≡C—, —CH₂O—, —OCH₂—, —COO—, or —OCO—; and

W is —CH₂—, —CO—, or —CF₂—.

A more preferable example of the compound (a) is any one of thecompounds (a-1-1) to (a-1-6) and the compounds (a-2-1) to (a-2-6). Thecompound is more stable chemically, and has liquid crystal phases in awider temperature range, a smaller viscosity, a suitable opticalanisotropy, a large negative dielectric anisotropy, a suitable elasticconstant K₃₃, and an excellent compatibility with other liquid crystalcompounds by the effect of such a structure. Moreover, a compositionwhich includes the compound has a higher maximum temperature of anematic phase. In particular, the composition is excellent, because itis more stable chemically, and has liquid crystal phases in a widertemperature range and smaller viscosity.

When W is —CH₂— in formulas (a-1-1) to (a-1-6) and in formulas (a-2-1)to (a-2-6), the compound is desirable, because the stability of thecompound is higher, and the dielectric anisotropy is larger andnegative. When W is —CO—, the compound is desirable, because thetemperature range of liquid crystal phases is wider, compatibility withother liquid crystal compounds is better, and the maximum temperature ofa nematic phase of a composition which include the compound is higher.When W is —CF₂—, the compound is desirable, because the compatibilitywith other liquid crystal compounds is superior to other groups.

In formulas (a-1-1) to (a-1-6) and formulas (a-2-1) to (a-2-6), Ra¹ andRb¹ are each independently alkyl having 1 to 12 carbons, alkoxy having 1to 11 carbons, or alkenyl having 2 to 12 carbons; and

W is —CH₂—, —CO—, or —CF₂—.

As described above, the compound having objective physical propertiescan be obtained by suitably selecting the kinds of terminal groups, ringstructures, and bonding groups, and the number of rings. Accordingly,the compound (a) can be suitably applied to liquid crystal compositionsused for liquid crystal devices with display modes such as PC, TN, STN,ECB, OCB, IPS, VA, and PSA, and especially to liquid crystalcompositions used for liquid crystal display devices with display modessuch as IPS, VA, and PSA.

The compound (a) that the structure is disclosed in this specificationcan be synthesized by suitably combining techniques in synthetic organicchemistry. Methods for introducing objective terminal groups, ringstructures, and bonding groups into starting materials are described inbooks such as ORGANIC SYNTHESES (John Wiley & Sons, Inc), ORGANICREACTIONS (John Wiley & Sons, Inc), COMPREHENSIVE ORGANIC SYNTHESIS(Pergamon Press), and NEW EXPERIMENTAL CHEMISTRY COURSE (Shin JikkenKagaku Kouza, in Japanese title) (Maruzen).

<Formation of the Bonding Group Z¹ or Z²>

Examples of methods for forming the bonding group Z¹ or Z² will beshown. The scheme for forming the bonding group is shown below. In thisscheme, MSG¹ or MSG² is a monovalent organic group. A plurality of MSG¹(or MSG²) used in the scheme may be the same or different. The compounds(1A) to (1I) correspond to the liquid crystal compound (a)

<Formation of Single Bonds, Part 1>

The compound, which is obtained by treating the organohalogen compound(a1) having the monovalent organic group MSG¹ with butyl lithium ormagnesium, is reacted with a boric acid ester such as trimethyl borate,and then hydrolyzed by an acid such as hydrochloric acid, giving thedihydroxyborane derivative (a2). Subsequently, the compound (1A) can besynthesized by reacting the resultant derivative (a2) with theorganohalogen compound (a3) having the monovalent organic group MSG² inthe presence, for example, of an aqueous carbonate solution andtetrakis(triphenylphosphine)palladium (Pd(PPh₃)₄).

The compound (1A) can also be synthesized by reacting the organichalogen compound (a1) with n-butyl lithium and further with zincchloride, and then reacting the compound obtained with the compound (a3)in the presence, for example, of abistriphenylphosphinedichloropalladium [PdCl₂(PPh₃)₂] catalyst.

<Formation of Single Bonds, Part 2>

A Grignard reagent or a lithium salt is prepared by reacting the organichalogen compound (a3) with magnesium or n-butyl lithium, respectively,or by reacting the compound (a5) with n-butyl lithium or sec-butyllithium. On reacting the Grignard reagent or the lithium salt with thecyclohexanone derivative (a4), the corresponding alcohol derivative issynthesized. Subsequently, the compound (1B) which is combined with thecyclohexene derivative through a single bond can be synthesized bydehydrating the alcohol derivative in the presence of an acid catalystsuch as p-toluenesulfonic acid. The compound (1C) having the cyclohexanederivative moiety bonded through a single bond can be synthesized byhydrogenating the compound (1B) thus obtained in the presence of acatalyst such as palladium on carbon (Pd/C). Incidentally, thecyclohexanone derivative (a4) can be synthesized, for example, accordingto the method described in JP S59-7122 A (1984).

<Formation of Double Bonds>

A Grignard reagent or a lithium salt is prepared by reacting theorganohalogen compound (a3) with magnesium or n-butyl lithium,respectively. An alcohol derivative is synthesized by reacting theGrignard reagent or the lithium salt with the aldehyde derivative (a6).Subsequently, the compound (1D) which has a corresponding double bondcan be synthesized by dehydrating the resultant alcohol derivative inthe presence of an acid catalyst such as p-toluenesulfonic acid.

A Grignard reagent or a lithium salt is prepared by reacting the organichalogen compound (a3) with magnesium or n-butyl lithium, respectively.The aldehyde derivative (a7) is obtained by reacting the Grignardreagent or lithium salt with a formamide such as N,N-dimethylformamide(DMF). Subsequently, the compound (1D) which has a corresponding doublebond can be synthesized by reacting the resultant aldehyde derivative(a7) with the phosphorus ylide obtained by treating the phosphonium salt(a8) with a base such as potassium t-butoxide. Since a cis-isomer may beformed depending on reaction conditions in the reaction described above,the cis-isomer is isomerized to a trans isomer according to knownmethods as requested.

<Formation of —(CH₂)₂—>

The compound (1E) can be synthesized by hydrogenating the compound (1D)in the presence of a catalyst such as palladium on carbon (Pd/C).

<Formation of —CH₂O— or —OCH₂—>

The alcohol derivative (a9) is obtained by oxidizing the dihydroxyboranederivative (a2) with an oxidizing agent such as hydrogen peroxide(H₂O₂). In a separate run, the alcohol derivative (a10) is obtained byreducing the aldehyde derivative (a7) with a reducing agent such assodium borohydride. The organohalogen compound (a11) is obtained byhalogenating the compound (a10) thus obtained with hydrobromic acid andso forth. The compound (1F) can be synthesized by reacting the compound(a9) thus obtained with the compound (a11) in the presence of potassiumcarbonate (K₂CO₃) or the like. The compound having —CH₂O— can also besynthesized according to this method.

<Formation of —COO— and —OCO—>

The compound (a1) is reacted with n-butyl lithium and then with carbondioxide giving the carboxylic acid derivative (a12). The compound (1G)having —COO— can be synthesized by reacting the carboxylic acidderivative (a12) with the alcohol derivative (a13) in the presence ofDDC (1,3-dicyclohexylcarbodiimide) and DMAP (4-dimethylaminopyridine).The compounds having —OCO— can also be synthesized according to thismethod.

<Formation of —CF₂O— and —OCF₂—>

The compound (a14) is obtained by treating the compound (1G) with athionating agent such as Lawesson's reagent. The compound (1H) having—CF₂O— can be synthesized by fluorinating the compound (a14) by use of ahydrogen fluoride-pyridine complex and NBS (N-bromosuccinimide). Referto M. Kuroboshi, et al., Chem. Lett., 1992, 827. The compound (1H) isalso synthesized by fluorinating the compound (a14) with(diethylamino)sulfur trifluoride (DAST). Refer to W. H. Bunnelle, etal., J. Org. Chem. 1990, 55, 768. These bonding groups can also beformed according to the method described in Peer. Kirsch, et al., Angew.Chem. Int. Ed. 2001, 40, 1480. The compound having —OCF₂— can also besynthesized according to this method.

<Formation of —C≡C—>

The compound (a15) is obtained by reacting the compound (a1) with2-methyl-3-butyne-2-ol in the presence of a catalyst ofdichloropalladium and copper halide, and then by deprotecting theresulting product under a basic condition. The compound (1I) can besynthesized by reacting the compound (a15) with the compound (a3) in thepresence of a catalyst of dichloropalladium (PdCl₂) and cuprous iodide(CuI).

[Method for Producing the Liquid Crystal Compound (a)]

Hereinafter a production example of the liquid crystal compound (b3) ,that is to say, the liquid crystal compound (a) wherein W is —CO— isshown. In the following reaction pathway, Ra, Rb, ring A¹, ring A², ringA³, ring A⁴, Z¹, Z², m, and n have the meanings identical to thosedescribed above.

The compound (b3) having an ester group, which is one example of theliquid crystal compound (a) of the invention, can be produced byreacting the carboxylic acid derivative (1) with the phenol derivative(b2) in the presence of DCC and DMAP.

Next, a production example of the liquid crystal compound (b7), that isto say, the liquid crystal compound (a) wherein W is —CH₂— is shown. Inthe following reaction pathway, Ra, Rb, ring A¹, ring A², ring A³, ringA⁴, Z′, Z², m, and n have the meanings identical to those describedabove.

The methyl ester derivative (b4) is obtained by reacting the carboxylicacid derivative (b1) with methanol in the presence of a catalyst such asconcentrated sulfuric acid or the like. The alcohol derivative (b5) isobtained by reducing the compound (b4) obtained with a reducing agentsuch as lithium hydride aluminum (LiAlH₄). Subsequently, the compound(b6) is obtained by brominating the compound (b5) with carbontetrabromide (CBr₄) and triphenylphosphine (Ph₃P). The compound (b7)having a methyleneoxy group, which is an example of the liquid crystalcompound (a) of the invention, can be produced by etherifying thecompound (b6) obtained with the phenol derivative (b2) in the presenceof a base such as potassium carbonate.

Further, a production example of the liquid crystal compound (b3), thatis to say, the liquid crystal compound (a) wherein W is —CH₂— is shown.In the following reaction pathway, Ra, Rb, ring A¹, ring A², ring A³,ring A⁴, Z¹, Z², m, and n have the meanings identical to those describedabove.

The thioester derivative (b8) is derived from the carboxylic acidderivative (b1) by use of Lawesson's reagent. Subsequently, the compound(b8) obtained is fluorinated with HF-Py or the like in the presence ofNBS, producing the compound (b9) having a difluoromethyleneoxy group,which is one example of the liquid crystal compound (a) of theinvention.

[Liquid Crystal Compositions]

Hereinafter, the liquid crystal composition of the invention isexplained. This liquid crystal composition is characterized bycontaining at least one of the liquid crystal compound (a) as acomponent, and the composition may contain two or more of the liquidcrystal compound (a), or may be composed of the liquid crystal compound(a) only. When the liquid crystal composition of the invention isprepared, the components can also be selected in consideration of, forexample, dielectric anisotropy of the liquid crystal compound (a). Theliquid crystal composition described above has a low viscosity, asuitable and negative dielectric anisotropy, a suitable elastic constantK₃₃, a low threshold voltage, a high maximum temperature of a nematicphase (phase transition temperature of a nematic phase to isotropicphase), and a low minimum temperature of the nematic phase.

[The Liquid Crystal Composition (1)]

It is desirable that the liquid crystal composition of the inventionfurther includes at least one compound selected from the group of liquidcrystal compounds represented by formulas (e-1) to (e-3) (hereinafteralso referred to as the compounds (e-1) to (e-3)) as a second component,in addition to the liquid crystal compound (a) (hereinafter alsoreferred to as the liquid crystal composition (1)).

In formulas (e-1) to (e-3), Ra₁₁ and Rb₁₁ are each independently alkylhaving 1 to 10 carbons, and in this alkyl, —CH₂— may be nonadjacentlyreplaced by —O—, —(CH₂)₂— may be nonadjacently replaced by —CH═CH—, andhydrogen may be replaced by fluorine.

Ring A¹¹, ring A¹², ring A¹³, and ring A¹⁴ are each independently1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,3-fluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, ortetrahydropyran-2,5-diyl.

The symbols Z¹¹, Z¹², and Z¹³ are each independently a single bond,—CH₂CH₂—, —CH═CH—, —C≡C—, —COO—, or —CH₂O—.

Viscosity of a liquid crystal composition can be decreased, and theminimum temperature of a nematic phase can also be decreased by theaddition of the second component to the liquid crystal compound (a).Because the dielectric anisotropy of the compounds (e-1) to (e-3) isnearly 0, the dielectric anisotropy of the liquid crystal compositioncontaining the compound can be adjusted so as to approach 0.

The compound (e-1) or compound (e-2) is effective in decreasing theviscosity and increasing the voltage holding ratio of the liquid crystalcomposition including the compound. The compound (e-3) is effective inincreasing the maximum temperature of a nematic phase and increasing thevoltage holding ratio of the liquid crystal composition including thecompound.

In ring A¹¹, ring A¹², ring A¹³, and ring A¹⁴, when two or more ringsare 1,4-cyclohexylene, the maximum temperature of a nematic phase of theliquid crystal composition including them is higher, and when two ormore rings are 1,4-phenylene, the optical anisotropy of the compositionincluding them is larger.

More desirable compounds among the second component are the compoundsrepresented by formulas (2-1) to (2-74) (hereinafter also referred to asthe compounds (2-1) to (2-74)). In these compounds, Ra₁₁ and Rb₁₁ havethe meanings identical to those described for the compounds (e-1) to(e-3).

When the second component is the compounds (2-1) to (2-74), a liquidcrystal composition which is excellent in heat resistance and lightresistance and has a higher voltage holding ratio, a small viscosity,and a nematic phase in a wide range can be prepared.

In particular, the liquid crystal composition (1) in which the firstcomponent is at least one compound selected from the group of compoundsrepresented by formulas (a-1-1) to (a-1-6) and formulas (a-2-1) to(a-2-6) and the second component is at least one compound selected fromthe group of compounds represented by the compounds (e-1) to (e-3) isparticularly excellent in heat resistance and light resistance, and hasa nematic phase in a wider range, a larger voltage holding ratio, asmaller viscosity, and a suitable elastic constant K₃₃.

The content of the second component in the liquid crystal composition(1) of the invention is not limited particularly, and it is desirable toincrease the content in view of a lower viscosity. However, thethreshold voltage of the liquid crystal composition tends to increasewith an increase the content of the second component, because theabsolute value of the dielectric anisotropy is decreased. Accordinglythe content of the second component is preferably in the range of 40% to95% by weight, and the content of the first component is preferably 5%to 60% by weight, based on the total weight of the liquid crystalcompounds contained in the liquid crystal composition (1), when theliquid crystal composition of the invention is used for a liquid crystaldevice having a VA mode.

[The Liquid Crystal Composition (2)]

A liquid crystal composition which further includes at least onecompound selected from the group of liquid crystal compounds representedby formulas (g-1) to (g-6) (hereinafter also referred to as thecompounds (g-1) to (g-6)) as a third component in addition to the firstand second components, is also desirable as a liquid crystal compositionof the invention (hereinafter also referred to as the liquid crystalcomposition (2)).

In formulas (g-1) to (g-6), Ra₂₁ and Rb₂₁ are each independentlyhydrogen or alkyl having 1 to 10 carbons, and in this alkyl, —CH₂— maybe nonadjacently replaced by —O—, —(CH₂)₂— may be nonadjacently replacedby —CH═CH—, and hydrogen may be replaced by fluorine.

In formulas (g-1) to (g-6), ring A²¹, ring A²², and ring A²³ are eachindependently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,3-fluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, ortetrahydropyran-2,5-diyl.

In formulas (g-1) to (g-6), Z²¹, Z²², Z²³ are each independently asingle bond, —(CH₂)₂—, —CH═C—, —C≡C—, —OCF₂—, —CF₂O—, —OCF₂CH₂CH₂—,—CH₂CH₂CF₂O—, —COO—, —OCH₂—, or —CH₂O—, and Y¹, Y², Y³, and Y⁴ are eachindependently fluorine or chlorine.

In formulas (g-1) to (g-6), q, r, and s are each independently 0, 1, or2, q+r+s is 1, 2, or 3, and t is 0, 1, or 2. When q, r, and s are 2 or3, a plurality of ring A²¹, ring A²², ring A²³, Z²¹, Z²²,and Z²³ may bethe same or different.

The liquid crystal composition (2) which further includes the thirdcomponent has a large negative dielectric anisotropy. Moreover, theliquid crystal composition has a wide temperature range of a nematicphase, a small viscosity, a large negative dielectric anisotropy, and alarge specific resistance value, and these physical properties aresuitably balanced.

Among the third component, the compound (g-1) or the compound (g-2) candecrease viscosity. In view of a low viscosity, heat resistance, andlight resistance, at least one compound selected from the group ofcompounds represented by formulas (h-1) to (h-7) (hereinafter alsoreferred to as the compounds (h-1) to (h-7)) is desirable.

In formulas (h-1) to (h-7), Ra₂₂ and Rb₂₂ are a straight-chain alkylhaving 1 to 8 carbons, a straight-chain alkenyl having 2 to 8 carbons,or alkoxy having 1 to 7 carbons, Z²⁴, Z²⁵, and Z²⁶ are a single bond,—(CH₂)₂—, —CH₂O—, —OCH₂—, —COO—, or —OCO—, and Y¹ and Y² aresimultaneously fluorine, or one of Y¹ and Y² is fluorine and the otheris chlorine.

For example, the compound (h-1) or compound (h-2) can decrease theviscosity, decrease the threshold voltage value, and decrease theminimum temperature of a nematic phase in the liquid crystal compositionincluding the compound. The compounds (h-2) or (h-3), or the compound(h-4) can decrease the threshold voltage value without decreasing themaximum temperature of a nematic phase in the liquid crystal compositionincluding the compound.

The compound (h-3) and the compound (h-6) can increase opticalanisotropy, and the compound (h-4) and the compound (h-7) can furtherincrease optical anisotropy.

The compounds (h-5) or (h-6), or the compound (h-7) can decrease theminimum temperature of a nematic phase in the liquid crystal compositionincluding the compound.

Among the third components, the compounds (3-1) to (3-118) are moredesirable. In these compounds, Rb₂₂ and Rb₂₂ have the meanings identicalto those described for the compounds (h-1) to (h-7).

For example, compounds having a condensed ring, such as the compounds(g-3) to (g-6) are desirable in view of decreasing a thresholdvoltage-value, and the compounds (3-119) to (3-143) are desirable inview of heat resistance or light resistance. In these compounds, Ra₂₂and Rb₂₂ have the meanings identical to those described for thecompounds (g-3) to (g-6).

Among the liquid crystal compositions (2), in particular, a liquidcrystal composition which includes first, second, and third componentshas an excellent heat resistance and light resistance, a widetemperature range of a nematic phase, a small viscosity, a high voltageholding ratio, a suitable optical anisotropy, a suitable dielectricanisotropy, and a suitable elastic constant K₃₃, wherein the firstcomponent is at least one compound selected from the group of compoundsrepresented by formulas (a-1-1) to (a-1-6) and formulas (a-2-1) to(a-2-6), the second component is at least one compound selected from thegroup of compounds represented by formulas (e-1) to (e-3), and the thirdcomponent is at least one compound selected from the group of compoundsrepresented by formulas (h-1) to (h-7). Furthermore, the liquid crystalcomposition is desirable in view of these physical properties suitablybalanced.

The content of the third component in the liquid crystal composition ofthe invention is not limited particularly, and it is desirable toincrease the content in view of preventing a decrease in the absolutevalue of a negative dielectric anisotropy. Although the content ratiosof the first, second, and third components of the liquid crystalcomposition (2) of the invention are not limited particularly, it isdesirable that the content ratio of the liquid crystal compound (a) isin the range of 5% to 60% by weight, the content ratio of the secondcomponent is in the range of 20% to 75% by weight, and the content ratioof the third component is in the range of 20% to 75% by weight based onthe total weight of the liquid crystal composition (2).

When the ratios of the contents of the first, second, and thirdcomponents of the liquid crystal composition (2) are in the rangesdescribed above, the composition (2) has an excellent heat resistanceand light resistance, a wide temperature range of a nematic phase, asmall viscosity, a high voltage holding ratio, and a suitable opticalanisotropy, a suitable dielectric anisotropy, a suitable elasticconstant K₃₃. Furthermore, a liquid crystal composition in which thesephysical properties are more suitably balanced is obtained.

[Aspects and so forth of the Liquid Crystal Composition]

In one aspect on the liquid crystal composition of the invention, otherliquid crystal compounds, in addition to the liquid crystal compoundscomposed of the first and second components, and the third componentwhich is added as requested, may be added and used for the purpose offurther adjusting, for example, characteristics of the liquid crystalcomposition. In another aspect on the liquid crystal composition of theinvention, other liquid crystal compounds except the liquid crystalcompounds composed of the first and second components, and the thirdcomponent which is added as requested may not be added and used, forexample, in view of their cost.

Additives, such as an optically active compound, a coloring matter, anantifoaming agent, an ultraviolet absorber, an antioxidant, apolymerizable compound, and a polymerization initiator may further beadded to the liquid crystal composition of the invention. When theoptically active compound is added to the liquid crystal composition ofthe invention, it can induce a helical structure and giving a twistangle liquid crystals or something.

When the coloring matter is added to the liquid crystal composition ofthe invention, the liquid crystal composition can be applied to theliquid crystal display device having a GH (Guest host) mode.

When the antifoaming agent is added to the liquid crystal composition ofthe invention, it is possible to suppress the formation of foam duringthe transportation of the liquid crystal composition or in a process ofmanufacturing liquid crystal display devices using this liquid crystalcomposition.

When the ultraviolet absorber or the antioxidant is added to the liquidcrystal composition of the invention, it is possible to preventdegradation or something of the liquid crystal composition and of theliquid crystal display device containing the liquid crystal composition.When the liquid crystal composition is irradiated with ultravioletlight, for example, the ultraviolet absorber can suppress a decrease ofa voltage holding ratio or a specific resistance value by suppressingdecomposition of compounds. When the liquid crystal composition isheated, for example, the antioxidant can suppress a decrease of avoltage holding ratio and a specific resistance value by suppressingoxidation or decomposition of compounds.

Ultraviolet absorbers include a benzophenone-based ultraviolet absorber,a benzoate-based ultraviolet absorber, and a triazole-based ultravioletabsorber.

A specific example of the benzophenone-based ultraviolet absorber is2-hydroxy-4-n-octoxybenzophenone.

A specific example of the benzoate-based ultraviolet absorber is2,4-di-t-butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate.

Specific examples of the triazole-based ultraviolet absorber are2-(2-hydroxy-5-methylphenyl) benzotriazole,2-[2-hydroxy-3-(3,4,5,6-tetrahydroxyphthalimide-methyl)-5-methylphenyl]benzotriazole,and 2-(3-t-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole.

Antioxidants include a phenol-based antioxidant and anorganosulfur-based antioxidant.

Specific examples of the phenol-based antioxidant are2,6-di-t-butyl-4-methylphenol, 2,6-di-t-butyl-4-ethylphenol,2,6-di-t-butyl-4-propylphenol, 2,6-di-t-butyl-4-butylphenol,2,6-di-t-butyl-4-pentylphenol, 2,6-di-t-butyl-4-hexylphenol,2,6-di-t-butyl-4-heptylphenol, 2,6-di-t-butyl-4-octylphenol,2,6-di-t-butyl-4-nonylphenol, 2,6-di-t-butyl-4-decylphenol,2,6-di-t-butyl-4-undecylphenol, 2,6-di-t-butyl-4-dodecylphenol,2,6-di-t-butyl-4-tridecylphenol, 2,6-di-t-butyl-4-tetra-decylphenol,2,6-di-t-butyl-4-pentadecylphenol, 2,2′-methylenebis(6-t-butyl4-methylphenol), 4,4′-butylidenebis(6-t-butyl-3-methylphenol),2,6-di-t-butyl-4-(2-octadecyloxycarbonyl)ethylphenol, andpentaerythritol tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate].

Specific examples of the organosulfur-based antioxidant aredilauryl-3,3′-thiopropionate, dimyristyl-3,3′-thiopropionate,distearyl-3,3′-thiopropionate,pentaerythritoltetrakis(3-laurylthiopropionate), and2-mercaptobenzimidazole.

Additives typified by an ultraviolet absorber, antioxidant and so forthmay be added and used in the range of amounts which do not prevent thepurpose of the invention and can attain the purpose of the addition ofthe additives.

When an ultraviolet absorber or an antioxidant is added, for example,its content ratio is usually in the range of 10 ppm to 500 ppm,preferably in the range of 30 ppm to 300 ppm, and more preferably in therange of 40 ppm to 200 ppm based on the total weight of the liquidcrystal composition of the present invention.

Incidentally, in another aspect, the liquid crystal composition of theinvention may contain impurities of starting materials, by-products,solvents used for reactions, catalysts for syntheses and so forth, whichhave been contaminated in the processes, such as for synthesizing eachcompound constituting a liquid crystal composition, and for preparingthe liquid crystal composition.

A polymerizable compound is mixed into a composition in order to adjustthe composition to a device having the PSA (polymer sustained alignment)mode. A desirable example of the polymerizable compound is a compoundhaving a polymerizable group such as a acrylate, a methacrylate, a vinylcompound, a vinyloxy compound, a propenyl ether, or an epoxy compound. Aparticularly desirable example is an acrylate derivative or amethacrylate derivative. A desirable ratio of the polymerizable compoundis 0.05% by weight or more in order to achieve its effect and 10% byweight or less in order to avoid a poor display. A more desirable ratiois in the range of 0.1% to 2% by weight. The polymerizable compound ispolymerized on irradiation with ultraviolet light or the like,preferably in the presence of a suitable initiator such as aphoto-polymerization initiator. Suitable conditions for polymerizationand the suitable type and amount of the initiator are known to a personskilled in the art, and are described in the literature. For example,Irgacure 651 (registered trademark), Irgacure 184 (registeredtrademark), or Darocure 1173 (registered trademark) (Ciba Geigy AG),which is a photoinitiator, is suitable for radical polymerization. Thepolymerizable compound contains a photopolymerization initiatorpreferably in the range of 0.1% to 5% by weight, and more preferably inthe range of 1% to 3% by weight.

[Method for Producing Liquid Crystal Compositions]

When each of the compounds which is the components of the liquid crystalcomposition of the invention is a liquid, for example, the compositionis prepared by mixing and shaking the compounds. When the componentsinclude solids, the composition is prepared by mixing them, and thenshaking after the compounds have been heated and liquefied. Moreover,the liquid crystal composition of the invention can also be prepared bymeans of other known methods.

[Characteristics of Liquid Crystal Compositions]

Because the maximum temperature of a nematic phase can be adjusted to70° C. or above and the minimum temperature of the nematic phase can beadjusted to −20° C. or below in the liquid crystal composition of theinvention, the temperature range of the nematic phase is wide.Accordingly, the liquid crystal display device containing this liquidcrystal composition can be used in a wide temperature range.

In the liquid crystal composition of the invention, the opticalanisotropy can be in the range of 0.08 to 0.14, and preferably in therange of 0.05 to 0.18, by suitably adjusting the composition ratio andso forth. The dielectric anisotropy can be normally in the range of −5.0to −2.0, and preferably in the range of −4.5 to −2.5 in the liquidcrystal composition of the invention. The liquid crystal compositionhaving the dielectric anisotropy in these numerical ranges describedabove can be suitably used for a liquid crystal display device whichoperates by means of an IPS, VA, or PSA mode.

[Liquid Crystal Display Devices]

The liquid crystal composition of the invention can be used not only forthe liquid crystal display device having an operation mode such as a PC,TN, STN, OCB, or PSA mode which is driven by means of a AM mode, butalso for the liquid crystal display device having an operation mode suchas a PC, TN, STN, OCB, VA, and IPS mode which is driven by means of apassive matrix (PM) mode.

The liquid crystal display devices having the AM and PM mode can beapplied to liquid crystal displays and so forth having any of areflection type, a transmission type, and a semi-transmission type. Theliquid crystal composition of the invention can also be used for a DS(dynamic scattering) mode-device using the liquid crystal compositioninto which an conducting agent is added, a NCAP (nematic curvilinearaligned phase) device prepared by the method of microencapsulating theliquid crystal composition, and a PD (polymer dispersed) devicecontaining a three-dimensional network polymer formed in the liquidcrystal composition, for example, a PN (polymer network) device.

Because the liquid crystal composition of the present invention has thecharacteristics described above, it can be more suitably used for theliquid crystal display device having a AM mode which is operated bymeans of an operation mode, such as the VA, IPS, or PSA mode, whereinthe liquid crystal composition having a negative dielectric anisotropyis used, and especially for the liquid crystal display device having theAM mode which is driven by means of the VA mode.

The direction of an electric field is perpendicular to liquid crystallayers in a liquid crystal display device which is driven by means ofthe TN mode, the VA mode or the like. On the other hand, the directionof the electric field is parallel to liquid crystal layers in a liquidcrystal display device which is driven by means of the IPS mode or thelike. The structure of the liquid crystal display device which is drivenby means of the VA mode is reported by K. Ohmuro, S. Kataoka, T. Sasakiand Y. Koike, SID '97 Digest of Technical Papers, 28, 845 (1997), andthe structure of the liquid crystal display device which is driven bymeans of the IPS mode is reported in WO 1991/10936 A (patent family:U.S. Pat. No. 5,576,867).

[Example of the Liquid Crystal Compound (a)]

The invention will be explained below in more detail based on examples.However, the invention is not limited to the examples. The term “%”means “% by weight”, unless otherwise specified.

Because the compounds obtained were identified on the basis of nuclearmagnetic resonance spectra obtained by means of ¹H-NMR analysis, gaschromatograms obtained by means of gas chromatography (GC) analysis andso forth, the analytical methods will be explained first.

EXAMPLES ¹H-NMR Analysis:

A model DRX-500 apparatus (made by Bruker BioSpin Corporation) was usedfor measurement. Samples prepared in examples and so forth weredissolved in deuterated solvents such as CDCl₃ in which the samples weresoluble, and measurement was carried out under the conditions of roomtemperature, twenty four times of accumulation, and 500 MHz. In theexplanation of the nuclear magnetic resonance spectra obtained, symbolss, d, t, q, and m stand for a singlet, doublet, triplet, quartet, andmultiplet, respectively. Tetramethylsilane (TMS) was used as a standardreference material for a zero-point on chemical shift δ values.

GC Analysis:

A gas chromatograph Model GC-14B made by Shimadzu Corporation was usedfor measurement. A capillary column CBP1-M25-025 (length 25 m, bore 0.22mm, film thickness 0.25 μm; dimethylpolysiloxane as a stationary liquidphase; non-polar) made by Shimadzu Corporation was used. Helium was usedas a carrier gas, and its flow rate was adjusted to 1 ml per minute. Thetemperature of the sample injector was set at 300° C. and thetemperature of the detector (FID) was set at 300° C.

A sample was dissolved in toluene giving a 1% by weight solution, andthen 1 μl of the solution obtained was injected into the sampleinjector. Chromatopac Model C-R6A made by Shimadzu Corporation or itsequivalent was used as a recorder. The resulting gas chromatogramindicated the retention time of peaks and the values of peak areascorresponding to component compounds.

Chloroform or hexane, for example, may also be used as a solvent fordiluting the sample. The following capillary columns may also be used:DB-1 (length 30 m, bore 0.25 mm, film thickness 0.25 μm) made by AgilentTechnologies Inc., HP-1 (length 30 m, bore 0.32 mm, film thickness 0.25μm) made by Agilent Technologies Inc., Rtx-1 (length 30 m, bore 0.32 mm,film thickness 0.25 μm) made by Restek Corporation, BP-1 (length 30 m,bore 0.32 mm, film thickness 0.25 μm) made by SGE International Pty.Ltd, and so forth.

The ratio of peak areas in the gas chromatogram corresponds to the ratioof component compounds. In general, the percentage by weight of eachcomponent compound in an analytical sample is not completely the samewith the percentage of each peak area in the analytical sample. In theinvention, however, the percentage by weight of the component compoundin the analytical sample corresponds substantially to the percentage ofthe peak area in the analytical sample, because the correctioncoefficient is essentially 1 (one) when the columns described above areused. This is because there is no significant difference among thecorrection coefficients of liquid crystal compounds as components. Aninternal standard method by use of gas chromatograms is used in order todetermine the composition ratio of the liquid crystal compounds in theliquid crystal composition more accurately by means of gaschromatograms. The components of each liquid crystal compound(test-component) weighed accurately in a fixed amount and a liquidcrystal compound serving as a standard (standard reference material) areanalyzed simultaneously by means of gas chromatography, and the relativeintensity on the ratio of the peak area of the test-component to that ofthe standard reference material is calculated in advance. Next, thecomposition ratio of the liquid crystal compounds in the liquid crystalcomposition can be determined more accurately by means of thegas-chromatographic analysis using the correction based on the relativeintensity of the peak area of each component to that of the standardreference material.

[Samples for Measuring Physical Property-Values of Liquid CrystalCompounds and so forth]

Two kinds of samples are used for measuring the physical property-valuesof a liquid crystal compound: one is the compound itself, and the otheris a mixture of the compound and mother liquid crystals.

In the latter case using a sample in which a compound is mixed withmother liquid crystals, measurement is carried out according to thefollowing method. First, the sample is prepared by mixing 15% by weightof the liquid crystal compound obtained and 85% by weight of the motherliquid crystals. Then, extrapolated values are calculated from themeasured values of the resulting sample by means of an extrapolationmethod based on the following formula. The extrapolated values areregarded as the physical property-values of the compound.

(Extrapolated value)=[100×(Measured value of sample)−(% by weight ofmother liquid crystals}×(Measured value of mother liquid crystals)]/(%by weight of liquid crystal compound)

When a smectic phase or crystals are deposited even at this ratio of theliquid crystal compound to the mother liquid crystals at 25° C., theratio of the liquid crystal compound to the mother liquid crystals ischanged in the order of (10% by weight: 90% by weight), (5% by weight:95% by weight), and (1% by weight: 99% by weight). The physicalproperty-values of the sample are measured at the ratio in which thesmectic phase or the crystals are not deposited at 25° C. Extrapolatedvalues are determined according to the above equation, and regarded asthe physical property-values of the liquid crystal compound.

There are a variety of mother liquid crystals used for the measurementand, for example, the composition ratio (% by weight) of the motherliquid crystals (i) is as shown below. Mother Liquid Crystals (i):

[Method for Measuring Physical Property-Values of Liquid CrystalCompounds and so forth]

Physical property-values were measured according to the followingmethods. Most of the measurement methods were described in the Standardof Electronic Industries Association of Japan, EIAJ·ED-2521A, or thosewith some modifications. No TFT was attached to a TN device used formeasurement.

In regard to the measured values, in the case where a sample was aliquid crystal compound itself, values obtained, as they were, werereported herein as experimental data. In the case where the sample was amixture of the liquid crystal compound and mother liquid crystals,values obtained by extrapolating measured values were reported herein asexperimental data.

Phase Structure and Transition Temperature (° C.):

Measurement was carried out according to the following methods (1) and(2).

(1) A compound was placed on a hot plate of a melting point apparatus(Hot Stage Model FP-52 made by Mettler Toledo International Inc.)equipped with a polarizing microscope, and phase conditions and theirchanges were observed with the polarizing microscope, specifying thekinds of liquid crystal phases while the compound was heated at the rateof 3° C. per minute.(2) A sample was heated and then cooled at a rate of 3° C. per minute byuse of a Perkin-Elmer differential scanning calorimeter, a DSC-7 Systemor a Diamond DSC System. A starting point of an endothermic peak or anexothermic peak caused by a phase change of the sample was obtained bymeans of the extrapolation (on set) and the phase transition temperaturewas determined.

Hereinafter, the symbol C stood for crystals, which were expressed byCr₁ or Cr₂ when the kinds of crystals were distinguishable. The symbolsSm and N stood for a smectic phase and a nematic phase, respectively.The symbol Iso stood for a liquid (isotropic). When the differencebetween a smectic B phase and a smectic A phase was distinguishable inthe smectic phases, they were expressed as SmB, or SmA respectively.Transition temperatures were expressed as, for example, “C 50.0 N 100.0Iso”, which means that the transition temperature from crystals to anematic phase (CN) is 50.0° C., and the transition temperature from thenematic phase to a liquid (NI) is 100.0° C. The same applied to othertransition temperatures.

Maximum Temperature of Nematic Phase (T_(NI); ° C.):

A sample (a liquid crystal composition or a mixture of a liquid crystalcompound and mother liquid crystals) was placed on a hot plate of amelting point apparatus (Hot Stage Model FP-52 made by Mettler ToledoInternational Inc.) equipped with a polarizing microscope, and wasobserved with the polarizing microscope while being heated at the rateof 1° C. per minute. A maximum temperature meant a temperature measuredwhen part of the sample began to change from a nematic phase to anisotropic liquid. Hereinafter, the maximum temperature of a nematicphase may simply be abbreviated to “maximum temperature.”

Compatibility at Low Temperature:

Samples were prepared by mixing a compound with mother liquid crystalsso that the amount of the liquid crystal compound became 20% by weight,15% by weight, 10% by weight, 5% by weight, 3% by weight, and 1% byweight, and placed in glass vials . After these glass vials had beenkept in a freezer at 0° C., −5° C., −10° C., or −20° C. for a certainperiod, they were observed whether or not crystals or a smectic phasehad been deposited.

Viscosity η; measured at 20° C.; mPa·s):

A mixture of a liquid crystal compound and mother liquid crystals wasmeasured by use of an E-type viscometer.

Optical Anisotropy (Refractive Index Anisotropy; measured at 25° C.;Δn).

Measurement was carried out by use of an Abbe refractometer with apolarizing plate attached to the ocular, using light at a wavelength of589 nm. The surface of a main prism was rubbed in one direction, andthen a sample (a mixture of a liquid crystal compound and mother liquidcrystals) was dropped onto the main prism. A refractive index (n∥) wasmeasured when the direction of polarized light was parallel to that ofthe rubbing. A refractive index (n⊥) was measured when the direction ofpolarized light was perpendicular to that of the rubbing. The value ofoptical anisotropy was calculated from the equation: Δn=n∥−n⊥.

Dielectric Anisotropy (Δε; measured at 25° C.):

An ethanol solution (20 mL) of octadecyltriethoxysilane (0.16 mL) wasapplied to well-washed glass substrates. The glass substrates wererotated with a spinner, and then heated at 150° C. for 1 hour. A VAdevice in which a distance (cell gap) was 20 μm was assembled from thetwo glass substrates. A polyimide alignment film was prepared on glasssubstrates in a similar manner. After a rubbing-treatment to thealignment film obtained of the glass substrates, a TN device in which adistance between the two glass substrates was 9 μm and the twist anglewas 80 degrees was assembled.

A sample (a liquid crystal composition or a mixture of a liquid crystalcompound and mother liquid crystals) was put in the VA device obtained,applied with a voltage of 0.5 V (1 kHz, sine waves), and then adielectric constant (ε∥) in a major axis direction of liquid crystalmolecules was measured. The sample (the liquid crystal composition orthe mixture of the liquid crystal compound and the mother liquidcrystals) was put in the TN device obtained, applied with a voltage of0.5 V (1 kHz, sine waves), and then a dielectric constant (ε⊥) in aminor axis direction of liquid crystal molecules was measured. The valueof dielectric anisotropy was calculated from the equation of ε=ε∥−ε⊥.

Voltage Holding Ratio (VHR; measured at 25° C.; %):

A TN device used for measurement had a polyimide-alignment film and adistance between two glass substrates (cell gap) of 6 μm. A sample wasput in the device, and then the device was sealed with an adhesivepolymerizable under ultraviolet radiation. The TN device was charged at25° C. by applying pulse voltage (60 microseconds at 5 V). Decayingvoltage was measured for 16.7 milliseconds with a high speed voltmeter,and the area A between a voltage curve and a horizontal axis in a unitperiod was measured. The area B was an area without the voltage decay.The voltage holding ratio was the percentage of the area A to the areaB.

Elastic Constant (K₁₁ and K₃₃; measured at 25° C.):

An elastic constant measurement system Model EC-1 made by ToyoCorporation was used for measurement. A sample was put in a homeotropiccell in which a distance between two glass substrates (cell gap) was 20μm. An electric charge of 20 volts to 0 volts was applied to the cell,and electrostatic capacity and applied voltage were measured. Themeasured values of the electric capacity (C) and the applied voltage (V)were fitted to formula (2.98) and formula (2.101) in page 75 of the“Liquid crystal device handbook” (The Nikkan Kogyo Shimbun, LTD.) andthe value of the elastic constant was obtained from formula (2.100).

Example 1 Synthesis oftrans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl) phenoxymethyl]-trans-4-pentylbicyclohexyl (No. 1-1-23)

First Step:

trans-4′-Pentylbicyclohexyl-trans-4-carboxylic acid (1) (100.0 g),methanol (300 ml), and 95% sulfuric acid (1.0 g) were put in a reactionvessel and stirred under reflux for 2 hours. After completion of thereaction had been confirmed by means of gas chromatographic analysis,the reaction mixture was cooled to room temperature, toluene (600 ml)and water (900 ml) were added thereto, and mixed. The mixture wasallowed to stand until it had separated into an organic phase and anaqueous phase, and then an extractive operation into an organic phasewas carried out. The organic phases combined were sequentially washedwith water, an aqueous 1-N sodium hydroxide solution, and a saturatedaqueous solution of sodium hydrogencarbonate, dried over anhydrousmagnesium sulfate, and then concentrated under reduced pressure givingthe residue. The residue obtained was purified with a fractionaloperation by means of column chromatography using heptane as the fluentand silica gel as the stationary phase powder, and dried, giving 102.5 gof trans-4′-pentylbicyclohexyl-trans-4-carboxylic acid methylester (2).The yield based on the compound (1) was 97.4%.

Second Step:

Lithiumaluminumhydride (6.4 g) was suspended in THF (500 ml). Thecompound (2) (100.0 g) was added dropwise in the temperature range of 3°C. to 10° C. to this suspension, and the mixture was stirred for another2 hours in this temperature range. After completion of the reaction hadbeen confirmed by means of gas chromatographic analysis, ethyl acetateand a saturated aqueous ammonia solution were sequentially added to thereaction mixture on an ice bath, and the deposit was removed byfiltration through celite. The filtrate was extracted with ethylacetate. The organic phase obtained was sequentially washed with waterand saturated brine, and dried over anhydrous magnesium sulfate. Thesolution was concentrated under reduced pressure, giving 85.3 g of acrude compound containing (trans-4′-pentylbicyclohexyl-trans-4-yl)methanol (3). The crude compound obtained was a colorless solid.

Third Step:

The crude compound obtained in the second step (85.3 g) andtriphenylphosphine (133.8 g) were dissolved in methylene chloride (400ml). To this solution, a solution of carbon tetrabromide (169.1 g) inTHF (300 ml) was slowly added dropwise at room temperature, and themixture was stirred at room temperature for another 3 hours. Saturatedaqueous solution of sodium hydrogencarbonate and ethyl acetate wereadded to the reaction mixture obtained, and mixed. Then, the mixture wasallowed to stand until it had separated into an organic phase and anaqueous phase, and an extractive operation to an organic phase wascarried. The organic phase obtained was sequentially washed with water,saturated brine, and dried over anhydrous magnesium sulfate, and thenconcentrated under reduced pressure giving the residue. The residue wasa light yellow solid. The residue obtained was purified with afractional operation by means of column chromatography using n-heptaneas the eluent and silica gel as the stationary phase powder, and dried,giving 82.3 g of trans-4′-bromomethyl-trans-4-pentyl-bicyclohexyl (4).The compound (4) obtained was a colorless solid. The yield based on thecompound (2) was 73.6%.

Fourth Step

1-Ethoxy-2,3-difluoro-4-(trans-4-propylcyclohexyl)benzene (5) (50.0 g),48% hydrobromic acid (44.8 g), and glacial acetic acid (250 ml) were putin a reaction vessel, and stirred under reflux for 64 hours. Aftercompletion of the reaction had been confirmed by means of gaschromatographic analysis, the reaction mixture was cooled to 30° C.Water (500 ml) and toluene (500 ml) were added to the solution obtained,and mixed. Then, the mixture was allowed to stand until it had separatedinto an organic phase and an aqueous phase, and an extractive operationinto an organic phase was carried out. The organic phase obtained wasfractionated, washed with brine, and dried over anhydrous magnesiumsulfate. The solvent was then distilled off under reduced pressure, andthe residue obtained was purified by recrystallization from heptane anddried, giving 41.8 g of 2,3-difluoro-4-(trans-4-propylcyclohexyl)phenol(6). The yield based on the compound (5) was 92.9%.

The compound (5) can also be synthesized by the method described inJapanese Patent 2,811,342 B2 (1998) or the like.

Fifth Step:

The compound (4) (4.9 g), the compound (6) (4.0 g), tripotassiumphosphate n-hydrate (4.8 g), and DMF (30 ml) were put in a reactionvessel, and stirred at 70° C. for another 5 hours. After completion ofthe reaction had been confirmed by means of gas chromatographicanalysis, the reaction mixture was cooled to 30° C., and toluene (70 ml)and water (100 ml) were added to the mixture obtained, and mixed. Then,the mixture was allowed to stand until it had separated into an organicphase and an aqueous phase, and an extractive operation into an organicphase was carried out. The organic phase obtained was fractionated,washed with brine, and dried over anhydrous magnesium sulfate. Thesolvent was then distilled off under reduced pressure, and the residueobtained was purified with a fractional operation by means of columnchromatography using a mixed solvent of heptane and toluene (mixingratio; heptane:toluene=4:1) as the eluent and silica gel as thestationary phase powder. The residue was purified by recrystallizationfrom a mixed solvent of Solmix A-11 and heptane (volume ratio; SolmixA-11:heptane=1:2), and dried, giving 4.0 g oftrans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl)phenoxymethyl]-trans-4-pentylbicyclohexyl(No. 1-1-23). The yield based on the compound (4) was 53.6%.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified astrans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl)phenoxymethyl]-trans-4-pentylbicyclohexyl.The measurement solvent was CDCl₃.

Chemical shifts δ (ppm); 6.82(t, 1H), 6.64(t, 1H), 3.78(d, 2H), 2.73(tt,1H), 1.93-1.69(m, 13H), and 1.46-0.80(m, 34H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-1-23) were as follows.

Transition temperature: Cr 90.5 SmB 104.3 SmA 128.2 N 234.1 Iso.

T_(NI)=217.9° C., Δε=−4.5, Δn=0.109.

Example 2 Synthesis oftrans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl)phenoxymethyl]-trans-4-ethylbicyclohexyl(No. 1-1-8)

trans-4′-Ethylbicyclohexyl-trans-4-carboxylic acid was used instead ofthe compound (1), andtrans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl)phenoxymethyl]-trans-4-ethylbicyclohexyl(No. 1-1-8) was synthesized according to the procedure shown in Example1.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified astrans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl)phenoxymethyl]-trans-4-ethylbicyclohexyl.The measurement solvent was CDCl₃.

Chemical shift δ (ppm); 6.82(t, 1H), 6.64(t, 1H), 3.78(d, 2H), 2.73(tt,1H), 1.93-1.70(m, 13H), and 1.46-0.80(m, 28H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy ΔAn). The physical property-values ofthe compound (No. 1-1-8) were as follows.

Transition temperature: Cr 106.3 N 220.8 Iso.

T_(NI)=211.9° C., Δε=−5.3, Δn=0.112.

Example 3 Synthesis oftrans-4′-[2,3-difluoro-4-(trans-4-pentylcyclohexyl)phenoxymethyl]-trans-4-propylbicyclohexyl(No. 1-1-15)

trans-4′-[2,3-Difluoro-4-(trans-4-pentylcyclohexyl)-phenoxymethyl]-trans-4-propylbicyclohexyl(No. 1-1-15) was synthesized according to the procedure shown in Example1, using trans-4′-propylbicyclohexyl-trans-4-carboxylic acid instead ofthe compound (1), and using1-ethoxy-2,3-difluoro-4-(trans-4-pentylcyclohexyl)benzene instead of thecompound (5).

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified astrans-4′-[2,3-difluoro-4-(trans-4-pentylcyclohexyl)phenoxymethyl]-trans-4-propylbicyclohexyl.The measurement solvent was CDCl₃.

Chemical shift δ (ppm); 6.82(t, 1H), 6.64(t, 1H), 3.78(d, 2H), 2.73(tt,1H), 1.93-1.69(m, 13H), and 1.46-0.80(m, 34H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), dielectric anisotropy (Δε),and optical anisotropy (Δn). The physical property-values of thecompound (No. 1-1-15) were as follows.

Transition temperature: Cr 99.0 N 230.6 Iso.

T_(NI)=286.6° C., Δε=−6.1, Δn=0.127.

Example 4 Synthesis oftrans-4-[2,3-difluoro-4-(trans-4-vinylcyclohexylmethoxy)phenyl]-trans-4′-propylbicyclohexyl(No. 2-1-29)

First Step:

Under a nitrogen atmosphere, (trans-4-vinyl cyclohexyl) methanol (7)(12.0 g), imidazole (7.6 g), and triphenylphosphine (Ph₃P) (29.2 g) wereput in toluene (200 ml) and stirred at 5° C. Iodine (27.2 g) was dividedinto 10 parts and added thereto in the temperature range of 5 to 10° C.,and then stirred for another 3 hours . Completion of the reaction wasconfirmed by means of gas chromatographic analysis. The deposit wasremoved from the reaction mixture obtained by filtration, and thesolvent was distilled off from the filtrate under reduced pressure. Theresidue obtained was purified with a fractional operation by means ofcolumn chromatography using heptane as the eluent and silica gel as thestationary phase powder, and dried, giving 15.2 g of1-iodomethyl-trans-4-vinylcyclohexane (8). The yield based on thecompound (7) was 71.0%.

The compound (7) can be synthesized according to the method described inWO 2006/093102 A and so forth.

Second Step

Under a nitrogen atmosphere,trans-4′-(4-ethoxy-2,3-difluorophenyl)-trans-4′-propylbicyclohexyl (9)(30.3 g) was put in methylene chloride (300 ml), and stirred at −40° C.Boron tribromides (BBr₃) (25.0 g) were added thereto, and stirred at 0°C. for 20 hours. Completion of the reaction was confirmed by means ofgas chromatographic analysis. The reaction mixture obtained was pouredinto a vessel containing water (500 ml) cooled at 0° C. and methylenechloride (300 ml), and mixed. Then, the mixture was allowed to standuntil it had separated into an organic phase and an aqueous phase, andan extractive operation was carried out. The organic phase obtained wasfractionated, washed with brine, and dried over anhydrous magnesiumsulfate. The solvent was then distilled off under reduced pressure, andthe residue obtained was purified by recrystallization from a mixedsolvent of heptane and toluene (volume ratio; heptane and toluene=1:1),and dried, giving 27.0 g of2,3-difluoro-4-(trans-4′-propylbicyclohexyl-trans-4-yl)phenol (10). Theyield based on the compound (9) was 96.5%.

The compound (9) can be synthesized according to the method described inJapanese Patent No. 2,811,342 and so forth.

Third Step

Under a nitrogen atmosphere, compound (10) (1.7 g) and potassiumcarbonate (K₂CO₃) (0.83 g) were put in DMF (10 ml) and stirred at 70° C.The compound (8) (3.0 g) was added thereto and stirred at 70° C. foranother 4 hours. The reaction mixture obtained was cooled to 30° C., andtoluene (30 ml) and water (30 ml) were added, and mixed. Then, themixture was allowed to stand until it had separated into an organicphase and an aqueous phase, and an extractive operation into an organicphase was carried out. The organic phase obtained was fractionated,washed with brine, and dried over anhydrous magnesium sulfate. Thesolvent was then distilled off under reduced pressure, and the residueobtained was purified with a fractional operation by means of columnchromatography using a mixed solvent of heptane and toluene (volumeratio; heptane and toluene=4:1) as the eluent and silica gel as thestationary phase powder. The residue was purified by recrystallizationfrom a mixed solvent of Solmix A-11 and heptane (volume ratio; SolmixA-11:heptane=1:2), and dried, giving 0.9 g oftrans-4-[2,3-difluoro-4-(trans-4-vinylcyclohexylmethoxy)phenyl]-trans-4′-propylbicyclohexyl(No. 2-1-29). The yield based on the compound (10) was 39.2%.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified astrans-4-[2,3-difluoro-4-(trans-4-vinylcyclohexylmethoxy)phenyl]-trans-4′-propylbicyclohexyl.The measurement solvent was CDCl₃.

Chemical shift δ (ppm); 6.82(t, 1H), 6.65(t, 1H), 5.82-5.75(m, 1H),4.97(dt, 1H), 4.91(dt, 1H), 3.81(d, 2H), 2.71(tt, 1H), 1.95-1.71(m,14H), 1.41(q, 2H), 1.35-1.27(m, 2H), 1.20-0.95(m, 13H), and 0.89-0.82(m,5H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 2-1-29) were as follows.

Transition temperature: Cr₁ 69.9 Cr₂ 80.8 SmB 96.3 SmA 123.1 N 252.6Iso.

T_(NI)=215.9° C., Δε=−5.2, Δn=0.114.

Example 5 Synthesis oftrans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl)phenoxymethyl]-trans-4-vinylbicyclohexyl(No. 1-1-29)

trans-4′-[2,3-Difluoro-4-(trans-4-propylcyclohexyl)-phenoxymethyl]-trans-4-vinylbicyclohexyl(No. 1-1-29) was synthesized according to the procedure shown in Example4, using (trans-4′-vinylbicyclohexyl-trans-yl) methanol instead of thecompound (7) and using the compound (6) instead of the compound (10).

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified astrans-4′-[2,3-difluoro-4-(trans-4-propylcyclohexyl)phenoxymethyl]-trans-4-vinylbicyclohexyl.The measurement solvent was CDCl₃.

Chemical shift δ (ppm); 6.82(t, 1H),6.64(t, 1H), 5.81-5.74(m, 1H),4.95(d, 1H), 4.87(d, 1H), 3.78(d, 2H), 2.73(tt, 1H), 1.94-1.76(m, 14H),1.46-1.18(m, 7H), 1.10-1.04(m, 12H), and 0.90(t, 3H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-1-29) were as follows.

Transition temperature: Cr 96.1 N 234.8 Iso.

T_(NI)=211.9° C., Δε=−5.3, Δn=0.115.

Example 6 Synthesis oftran-4-{4-[2,3-difluoro-4-(trans-4-pentyl-cyclohexyl)phenoxymethyl]phenyl}-trans-4′-propylbicyclohexyl(No. 1-1-399)

trans-4-{4-[2,3-Difluoro-4-(trans-4-pentylcyclohexyl)-phenoxymethyl]phenyl}-trans-4′-propylbicyclohexyl(No. 1-1-399) can be synthesized by selecting trans-4′-(4-bromomethyl-phenyl)-trans-4-propylbicyclohexyl (11) as an alkyl halide derivativeand 2,3-difluoro-4-(trans-4-pentylcyclohexyl) phenol (12) as a phenolderivative, according to a procedure similar to that shown in Example 1or 3.

Example 7

A variety of compounds were synthesized by use of corresponding startingmaterials according to the procedure shown in Examples 1 to 6, and thecompounds were confirmed to be objective.

trans-4′-[2,3-Difluoro-4-(trans-4-ethoxycyclohexyl)phenoxy-methyl]-trans-4-pentylbicyclohexyl(No. 1-1-27)

Chemical shift δ (ppm); 6.80(t, 1H), 6.64(t, 1H), 3.78(d, 2H), 3.55(q,2H), 3.29(tt, 1H), 2.73(tt, 1H), 2.15(d, 2H), 1.95-1.85(m, 4H),1.80-1.67(m, 7H), and 1.56-0.78(m, 29H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-1-27) were as follows.

Transition temperature: Cr 108.4 SmA 112.7 N 223.0 Iso.

T_(NI)=203.6° C., Δε=−6.1, Δn=0.113.

2,3-Difluoro-4-(trans-4′-pentylbicyclohexyl-trans-4-ylmethoxy)-4′-biphenyl(No. 1-1-203)

Chemical shift δ (ppm); 7.41(d, 2H), 7.24(d, 2H), 7.07(t, 1H), 3.85(d,2H), 2.62(t, 2H), 1.95(m, 2H), 1.79-1.64(m, 9H), 1.32-1.21(m, 6H),1.17-0.94(m, 14H), and 0.89-0.81(m, 5H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-1-27) were as follows.

Transition temperature: Cr 111.3 SmA 169.8 N 231.6 Iso.

T_(NI)=214.6° C., Δε=−4.71, Δn=0.167, η=53.7 mPa·s.

4′-Butoxy-2,3,3′-trifluoro-4-(trans-4′-propylbicyclohexyl-trans-4-ylmethoxy)-biphenyl(No. 1-1-209)

Chemical shift δ (ppm); 7.25-7.18(m, 2H), 7.05-6.98(m, 2H), 6.76(t, 1H),4.07(t, 2H), 3.84(d, 2H), 1.95(m, 2H), 1.85-1.70(m, 9H), 1.56-1.49(m,2H), 1.33-1.27(m, 2H), 1.15-1.13(m, 3H), 1.06-0.94(m, 11H), and0.89-0.81(m, 5H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), dielectric anisotropy (Δε),and optical anisotropy (Δn). The physical property-values of thecompound (No. 1-1-209) were as follows.

Transition temperature: Cr 86.8 SmA 179.8 N 235.5 Iso.

T_(NI)=214.6° C., Δε=−6.1, Δn=0.174.

4′-Butoxy-2,3,3′-trifluoro-4-(trans-4′-vinylbicyclohexyl-trans-4-ylmethoxy)-biphenyl(No. 1-1-214)

Chemical shift δ (ppm); 7.26-7.19(m, 2H), 7.05-6.99(m, 2H), 6.76(t, 1H),5.81-5.74(m, 1H), 4.96(d, 1H), 4.88(d, 1H), 4.07(t, 2H), 3.85(d, 2H),1.96-1.78(m, 12H), 1.56-1.49(m, 2H), and 1.12-0.98(m, 13H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-1-214) were as follows.

Transition temperature: Cr 91.7 SmA 151.0 N 230.4 Iso.

T_(NI)=206.6° C., Δε=−6.6, Δn=0.176.

trans-4-[2,3-Difluoro-4-(trans-4-pentylcyclohexylmethoxy)-phenyl]-trans-4′-propylbicyclohexyl(No. 2-1-23)

Chemical shift δ (ppm); 6.82(t, 1H), 6.64(t, 1H), 3.78(d, 2H), 2.71(tt,1H), 1.91-1.72(m, 13H), and 1.44-0.82(m, 34H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), dielectric anisotropy (Δε),and optical anisotropy (Δn). The physical property-values of thecompound (No. 1-1-23) were as follows.

Transition temperature: Cr 77.0 SmB 133.2 SmA 167.7 N 246.2 Iso.

T_(NI)=268.6° C., Δε=−6.9, Δn=0.141.

2,3-Difluoro-4-(trans-4-pentylcyclohexylmethoxy)-4′-(trans-4-propylcyclohexyl)biphenyl (No. 2-1-85)

Chemical shift δ (ppm); 7.42(d, 2H), 7.27(d, 2H), 7.07(t, 1H), 6.77(t,1H), 3.85(d, 2H), 2.50(tt, 1H), 1.93-1.77(m, 9H), 1.52-1.44(m, 2H),1.39-1.17(m, 14H), 1.10-1.03(m, 4H), and 0.99-0.87(m, 8H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 2-1-85) were as follows.

Transition temperature: Cr (50.7 SmX) 76.6 SmC 80.9 N 239.5 Iso.

T_(NI)=218.6° C., Δε=−5.0, Δn=0.167.

2,3-Difluoro-4- (trans-4-pentylcyclohexylmethoxy)-4″-propyl-[1,1′;4′,1″] terphenyltrans-4-propylcyclohexyl)biphenyl (No.2-1-143)

Chemical shift δ (ppm); 7.64(d, 2H), 7.55(t, 4H), 7.26(d, 2H), 7.12(t,1H), 6.79(t, 1H), 3.87(d, 2H), 2.64(t, 2H), 1.94-1.92(m, 2H),1.83-1.78(m, 3H), 1.73-1.66(m, 2H), 1.33-1.18(m, 9H), and 1.08(qd, 2H),1.00-0.88(m, 8H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), the and optical anisotropy (Δn). The physical property-values ofthe compound (No. 2-1-143) were as follows.

Transition temperature: Cr 112.0 N 252.4 Iso.

T_(NI)=232.6° C., Δε=−4.3, Δn=0.247.

Example 8

The compounds (No. 1-1-1) to (No. 1-1-410), and the compounds (No.2-1-1) to (No. 2-1-410), which are shown in Table 1 to Table 56, can besynthesized by a synthesis method which is similar to the methodsdescribed in Examples 1 to 7.

TABLE 1 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-1  CH₃

— — —

CH₃ 1-1-2  CH₃

— — —

C₂H₅ 1-1-3  CH₃

— — —

C₃H₇ 1-1-4  CH₃

— — —

C₄H₉ 1-1-5  CH₃

— — —

C₅H₁₁ 1-1-6  C₂H₅

— — —

CH₃ 1-1-7  C₂H₅

— — —

C₂H₅ 1-1-8  C₂H₅

— — —

C₃H₇ Cr 106.3 N 220.8 Iso T_(NI): 211.9° C., Δ ε: −5.3, Δ n: 0.1121-1-9  C₂H₅

— — —

C₄H₉ 1-1-10 C₂H₅

— — —

C₅H₁₁ 1-1-11 C₃H₇

— — —

CH₃ 1-1-12 C₃H₇

— — —

C₂H₅ 1-1-13 C₃H₇

— — —

C₃H₇ 1-1-14 C₃H₇

— — —

C₄H₉ 1-1-15 C₃H₇

— — —

C₅H₁₁ Cr 99.0 N 230.6 Iso T_(NI): 286.6° C., Δ ε: −6.1, Δ n: 0.127

TABLE 2 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-16 C₄H₉

— — —

CH₃ 1-1-17 C₄H₉

— — —

C₂H₅ 1-1-18 C₄H₉

— — —

C₃H₇ 1-1-19 C₄H₉

— — —

C₄H₉ 1-1-20 C₄H₉

— — —

C₅H₁₁ 1-1-21 C₅H₁₁

— — —

CH₃ 1-1-22 C₅H₁₁

— — —

C₂H₅ 1-1-23 C₅H₁₁

— — —

C₃H₇ Cr 90.5 SmB 104.3 SmA 128.2 N 234.1 Iso T_(NI): 217.9° C., Δ ε:−4.5, Δ n: 0.109 1-1-24 C₅H₁₁

— — —

C₄H₉ 1-1-25 C₅H₁₁

— — —

C₅H₁₁ 1-1-26 C₃H₇

— — —

OC₂H₅ 1-1-27 C₅H₁₁

— — —

OC₂H₅ Cr 108.4 SmA 112.7 N 223.0 Iso T_(NI): 203.6° C., Δ ε: −6.1, Δ n:0.113 1-1-28 C₂H₅O

— — —

OC₄H₉ 1-1-29 CH₂═CH

— — —

C₃H₇ Cr 96.1 N 234.8 Iso T_(NI): 211.9° C., Δ ε: −5.3, Δ n: 0.115 1-1-30CH₂═CH

— — —

C₅H₁₁

TABLE 3 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-31 CH₃CH═CH

— — —

C₃H₇ 1-1-32 CH₃CH═CH

— — —

C₅H₁₁ 1-1-33 CH₂═CHC₂H₄

— — —

C₃H₇ 1-1-34 CH₂═CHC₂H₄

— — —

C₅H₁₁ 1-1-35 C₃H₇CH═CH

— —

C₂H₅ 1-1-36 C₃H₇CH═CH

— — —

C₃H₇ 1-1-37 CH₃CH═CHC₂H₄

— — —

CH₃ 1-1-38 CH₃CH═CHC₂H₄

— — —

C₂H₅ 1-1-39 C₃H₇

— — —

CH═CH₂ 1-1-40 C₅H₁₁

— — —

CH═CH₂ 1-1-41 C₃H₇

— — —

CH═CHCH₃ 1-1-42 C₄H₉

— — —

CH═CHCH₃ 1-1-43 C₂H₅

— — —

C₂H₄CH═CH₂ 1-1-44 C₃H₇

— — —

C₂H₄CH═CH₂ 1-1-45 CH₃

— — —

CH═CHC₃H₇

TABLE 4 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-46 C₂H₅

— — —

CH═CHC₃H₇ 1-1-47 C₂H₅

— — —

C₂H₄CH═CHCH₃ 1-1-48 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-1-49 CH₂═CH

— — —

C₂H₄CH═CH₂ 1-1-50 CH₃CH═CH

— — —

CH═CH₂ 1-1-51 C₃H₇OCH₂

— — —

C₃H₇ 1-1-52 C₅H₁₁

— — —

OC₂H₄CH═CH₂ 1-1-53 C₃H₇

CH₂CH₂ — —

C₂H₅ 1-1-54 C₅H₁₁

CH₂CH₂ — —

C₃H₇ 1-1-55 C₃H₇

CH₂O — —

C₂H₅ 1-1-56 C₅H₁₁

OCH₂ — —

C₃H₇ 1-1-57 H

COO — —

C₄H₉ 1-1-58 C₇H₁₅

OCO — —

C₄H₉ 1-1-59 C₂H₅

CF₂O — —

C₆H₁₃ 1-1-60 CH₃

OCF₂ — —

C₂H₅

TABLE 5 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-61 CH₃

— — —

CH₃ 1-1-62 CH₃

— — —

C₂H₅ 1-1-63 CH₃

— — —

C₃H₇ 1-1-64 CH₃

— — —

C₄H₉ 1-1-65 CH₃

— — —

C₅H₁₁ 1-1-66 C₂H₅

— — —

CH₃ 1-1-67 C₂H₅

— — —

C₂H₅ 1-1-68 C₂H₅

— — —

C₃H₇ 1-1-69 C₂H₅

— — —

C₄H₉ 1-1-70 C₂H₅

— — —

C₅H₁₁ 1-1-71 C₃H₇

— — —

CH₃ 1-1-72 C₃H₇

— — —

C₂H₅ 1-1-73 C₃H₇

— — —

C₃H₇ 1-1-74 C₃H₇

— — —

C₄H₉ 1-1-75 C₃H₇

— — —

C₅H₁₁

TABLE 6 (1-1)

Physical property No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb values 1-1-76 C₄H₉

— — —

CH₃ 1-1-77 C₄H₉

— — —

C₂H₅ 1-1-78 C₄H₉

— — —

C₃H₇ 1-1-79 C₄H₉

— — —

C₄H₉ 1-1-80 C₄H₉

— — —

C₅H₁₁ 1-1-81 C₅H₁₁

— — —

CH₃ 1-1-82 C₅H₁₁

— — —

C₂H₅ 1-1-83 C₅H₁₁

— — —

C₃H₇ 1-1-84 C₅H₁₁

— — —

C₄H₉ 1-1-85 C₅H₁₁

— — —

C₃H₇ 1-1-86 C₂H₅O

— — —

C₄H₉ 1-1-87 C₅H₁₁

— — —

OC₂H₅ 1-1-88 C₂H₅O

— — —

OC₄H₉ 1-1-89 C₅H₁₁

— — —

C₃H₇ 1-1-90 C₃H₇

— — —

C₅H₁₁

TABLE 7 (1-1)

Physical property No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb values 1-1-91 C₂H₅

— — —

C₄H₉ 1-1-92 C₅H₁₁

— — —

C₂H₅ 1-1-93 CH₂═CH

— — —

C₃H₇ 1-1-94 CH₂═CH

— — —

C₅H₁₁ 1-1-95 C₃H₇CH═CH

— — —

C₂H₅ 1-1-96 C₃H₇CH═CH

— — —

C₃H₇ 1-1-97 C₃CH═CHC₂H₄

— — —

CH₃ 1-1-98 C₃CH═CHC₂H₄

— — —

C₂H₅ 1-1-99 C₃H₇

— — —

CH═CH₂ 1-1-100 C₅H₁₁

— — —

CH═CH₂ 1-1-101 C₃H₇

— — —

CH═CHCH₃ 1-1-102 C₅H₁₁

— — —

CH═CHCH₃ 1-1-103 C₂H₅

— — —

C₂H₄CH═CH₂ 1-1-104 C₃H₇

— — —

C₂H₄CH═CH₂ 1-1-105 CH₃

— — —

CH═CHC₃H₇

TABLE 8 (1-1)

Physical property No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb values 1-1-106 C₂H₅

— — —

CH═CHC₃H₇ 1-1-107 C₂H₅

— — —

C₂H₄CH═CHCH₃ 1-1-108 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-1-109 CH₂═CH

— — —

C₂H₄CH═CH₂ 1-1-110 CH₃CH═CH

— — —

CH═CH₂ 1-1-111 C₅H₁₁OCH₂

— — —

C₃H₇ 1-1-112 C₃H₇

— — —

OC₂H₄CH═CH₂ 1-1-113 C₄H₉

CH₂CH₂ — —

C₂H₅ 1-1-114 C₅H₁₁

CH₂CH₂ — —

C₃H₇ 1-1-115 C₃H₇

CH₂O — —

C₂H₅ 1-1-116 C₅H₁₁

OCH₂ — —

C₆H₁₃ 1-1-117 C₅H₁₁

COO — —

C₄H₉ 1-1-118 C₂H₅

OCO — —

C₄H₉ 1-1-119 C₂H₅

CF₂O — —

CH₃ 1-1-120 C₄H₉

OCF₂ — —

C₂H₅

TABLE 9 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-121 CH₃

— — —

CH₃ 1-1-122 CH₃

— — —

C₂H₅ 1-1-123 CH₃

— — —

C₃H₇ 1-1-124 CH₃

— — —

C₄H₉ 1-1-125 CH₃

— — —

C₅H₁₁ 1-1-126 C₂H₅

— — —

CH₃ 1-1-127 C₂H₅

— — —

C₂H₅ 1-1-128 C₂H₅

— — —

C₃H₇ 1-1-129 C₂H₅

— — —

C₄H₉ 1-1-130 C₂H₅

— — —

C₅H₁₁ 1-1-131 C₃H₇

— — —

CH₃ 1-1-132 C₃H₇

— — —

C₂H₅ 1-1-133 C₃H₇

— — —

C₃H₇ 1-1-134 C₃H₇

— — —

C₄H₉ 1-1-135 C₃H₇

— — —

C₅H₁₁

TABLE 10 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-136 C₄H₉

— — —

CH₃ 1-1-137 C₄H₉

— — —

C₂H₅ 1-1-138 C₄H₉

— — —

C₃H₇ 1-1-139 C₄H₉

— — —

C₄H₉ 1-1-140 C₄H₉

— — —

C₅H₁₁ 1-1-141 C₅H₁₁

— — —

CH₃ 1-1-142 C₅H₁₁

— — —

C₂H₅ 1-1-143 C₅H₁₁

— — —

C₃H₇ 1-1-144 C₅H₁₁

— — —

C₄H₉ 1-1-145 C₅H₁₁

— — —

C₃H₇ 1-1-146 C₂H₅O

— — —

C₄H₉ 1-1-147 C₅H₁₁

— — —

OC₂H₅ 1-1-148 C₂H₅O

— — —

OC₄H₉ 1-1-149 C₅H₁₁

— — —

C₃H₇ 1-1-150 C₃H₇

— — —

C₅H₁₁

TABLE 11 (1-1)

Physical property No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb values 1-1-151 C₂H₅

— — —

C₄H₉ 1-1-152 C₅H₁₁

— — —

C₂H₅ 1-1-153 CH₂═CH

— — —

C₃H₇ 1-1-154 CH₂═CH

— — —

C₅H₁₁ 1-1-155 CH₃CH═CH

— — —

C₂H₅ 1-1-156 CH₂═CHC₂H₄

— — —

C₃H₇ 1-1-157 C₃H₇CH═CH

— — —

C₄H₉ 1-1-158 CH₃CH═CHC₂H₄

— — —

C₂H₅ 1-1-159 C₃H₇

— — —

CH═CH₂ 1-1-160 C₅H₁₁

— — —

CH═CH₂ 1-1-161 C₃H₇

— — —

CH═CHCH₃ 1-1-162 C₄H₉

— — —

CH═CHCH₃ 1-1-163 C₃H₇

— — —

C₂H₄CH═CH₂ 1-1-164 C₃H₇

— — —

C₂H₄CH═CH₂ 1-1-165 C₄H₉

— — —

CH═CHC₃H₇

TABLE 12 (1-1)

Physical property No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb values 1-1-166 C₂H₅

— — —

CH═CHC₃H₇ 1-1-167 C₂H₅

— — —

C₂H₄CH═CHCH₃ 1-1-168 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-1-169 CH₂═CH

— — —

CH═CH₂ 1-1-170 CH₃CH═CH

— — —

C₂H₄CH═CH₂ 1-1-171 CH₃OCH₂

— — —

C₃H₇ 1-1-172 C₂H₅

— — —

OC₂H₄CH═CH₂ 1-1-173 C₃H₇

CH₂CH₂ — —

C₂H₅ 1-1-174 C₅H₁₁

CH₂CH₂ — —

C₃H₇ 1-1-175 C₃H₇

CH₂O — —

C₃H₇ 1-1-176 C₃H₇

OCH₂ — —

CH₃ 1-1-177 C₅H₁₁

COO — —

C₄H₉ 1-1-178 C₂H₅

OCO — —

C₃H₇ 1-1-179 C₂H₅

CF₂O — —

C₇H₁₅ 1-1-180 C₄H₉

OCF₂ — —

C₂H₅

TABLE 13 (1-1)

Physical property No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb values 1-1-181 CH₃

— — —

CH₃ 1-1-182 CH₃

— — —

C₂H₅ 1-1-183 CH₃

— — —

C₃H₇ 1-1-184 CH₃

— — —

C₄H₉ 1-1-185 CH₃

— — —

C₅H₁₁ 1-1-186 C₂H₅

— — —

CH₃ 1-1-187 C₂H₅

— — —

C₂H₅ 1-1-188 C₂H₅

— — —

C₃H₇ 1-1-189 C₂H₅

— — —

C₄H₉ 1-1-190 C₂H₅

— — —

C₅H₁₁ 1-1-191 C₃H₇

— — —

CH₃ 1-1-192 C₃H₇

— — —

C₂H₅ 1-1-193 C₃H₇

— — —

C₃H₇ 1-1-194 C₃H₇

— — —

C₄H₉ 1-1-195 C₃H₇

— — —

C₅H₁₁

TABLE 14 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-196 C₄H₉

— — —

CH₃ 1-1-197 C₄H₉

— — —

C₂H₅ 1-1-198 C₄H₉

— — —

C₃H₇ 1-1-199 C₄H₉

— — —

C₄H₉ 1-1-200 C₄H₉

— — —

C₅H₁₁ 1-1-201 C₅H₁₁

— —

CH₃ 1-1-202 C₅H₁₁

— — —

C₂H₅ 1-1-203 C₅H₁₁

— — —

C₃H₇ Cr 111.3 SmA 169.8 N 231.6 Iso T_(NI): 214.6° C., Δ ε: −4.7, Δ n:0.167, η: 53.7 mPa·s 1-1-204 C₅H₁₁

— — —

C₄H₉ 1-1-205 C₅H₁₁

— — —

C₅H₁₁ 1-1-206 C₂H₅O

— — —

C₄H₉ 1-1-207 C₅H₁₁

— — —

OC₂H₅ 1-1-208 C₅H₅O

— — —

OC₄H₉ 1-1-209 C₃H₇

— — —

OC₄H₉ Cr 86.8 SmA 179.8 N 235.5 Iso T_(NI): 214.6° C., Δ ε: −6.1, Δ n:0.174 1-1-210 C₅H₁₁

— — —

OC₂H₅

TABLE 15 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-211 C₃H₇

— — —

C₅H₁₁ 1-1-212 C₅H₁₁

— — —

C₂H₅ 1-1-213 C₄H₉O

— — —

C₃H₇ 1-1-214 CH₂═CH

— — —

OC₄H₉ Cr 91.7 SmA 151.0 N 230.4 Iso T_(NI): 206.6° C., Δ ε: −6.6, Δ n:0.176 1-1-215 CH₂═CH

— — —

C₂H₅ 1-1-216 CH₂═CHC₂H₄

— — —

C₃H₇ 1-1-217 CH₃CH═CH

— — —

CH₃ 1-1-218 CH₂═CHC₂H₄

— — —

C₂H₅ 1-1-219 C₃H₇CH═CH

— — —

C₃H₇ 1-1-220 CH₃CH═CHC₂H₄

— — —

C₄H₉ 1-1-221 CH₃

— — —

CH₂OC₃H₇ 1-1-222 C₄H₉

— — —

CH₂CH₂F 1-1-223 C₂H₅

— — —

CH═CHCH₃ 1-1-224 C₃H₇

— — —

CH═CHC₃H₇ 1-1-225 C₃H₇

— — —

C₂H₄CH═CH₂

TABLE 16 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-226 C₂H₅

— — —

C₂H₄CH═CH₂ 1-1-227 C₅H₁₁

— — —

C₂H₄CH═CHCH₃ 1-1-228 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-1-229 CH₂═CH

— — —

C₂H₄CH═CH₂ 1-1-230 CH₃CH═OH

— — —

C₂H₄CH═CH₂ 1-1-231 C₃H₇OCH₂

— — —

C₃H₇ 1-1-232 C₃H₇

— — —

OC₂H₄CH═CH₂ 1-1-233 C₅H₁₁

CH₂CH₂ — —

C₂H₅ 1-1-234 C₅H₁₁

CH₂CH₂ — —

C₃H₇ 1-1-235 C₃H₇

CH₂O — —

H 1-1-236 C₂H₅

OCH₂ — —

C₃H₇ 1-1-237 C₄H₉

COO — —

C₄H₉ 1-1-238 C₃H₇

OCO — —

C₂H₅ 1-1-239 C₇H₁₅

CF₂O — —

C₂H₅ 1-1-240 C₉H₁₉

OCF₂ — —

CH₃

TABLE 17 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-241 CH₃

— — —

CH₃ 1-1-242 CH₃

— — —

C₂H₅ 1-1-243 CH₃

— — —

C₃H₇ 1-1-244 CH₃

— — —

C₄H₉ 1-1-245 CH₃

— — —

C₅H₁₁ 1-1-246 C₂H₅

— — —

CH₃ 1-1-247 C₂H₅

— — —

C₂H₅ 1-1-248 C₂H₅

— — —

C₃H₇ 1-1-249 C₂H₅

— — —

C₄H₉ 1-1-250 C₂H₅

— — —

C₅H₁₁ 1-1-251 C₃H₇

— — —

CH₃ 1-1-252 C₃H₇

— — —

C₂H₅ 1-1-253 C₃H₇

— — —

C₃H₇ 1-1-254 C₃H₇

— — —

C₄H₉ 1-1-255 C₃H₇

— — —

C₅H₁₁

TABLE 18 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-256 C₄H₉

— — —

CH₃ 1-1-257 C₄H₉

— — —

C₂H₅ 1-1-258 C₄H₉

— — —

C₃H₇ 1-1-259 C₄H₉

— — —

C₄H₉ 1-1-260 C₄H₉

— — —

C₅H₁₁ 1-1-261 C₅H₁₁

— — —

CH₃ 1-1-262 C₅H₁₁

— — —

C₂H₅ 1-1-263 C₅H₁₁

— — —

C₃H₇ 1-1-264 C₅H₁₁

— — —

C₄H₉ 1-1-265 C₅H₁₁

— — —

C₅H₁₁ 1-1-266 C₂H₅O

— — —

C₄H₉ 1-1-267 C₅H₁₁

— — —

OC₂H₅ 1-1-268 C₂H₅O

— — —

OC₄H₉ 1-1-269 C₃H₇

— — —

OC₄H₉ 1-1-270 C₅H₁₁

— — —

OC₂H₅

TABLE 19 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-271 C₃H₇

— — —

C₅H₁₁ 1-1-272 C₃H₇O

— — —

C₅H₁₁ 1-1-273 C₅H₁₁

— — —

OC₂H₅ 1-1-274 CH₂═CH

— — —

C₅H₁₁ 1-1-275 CH₃CH═CH

— — —

C₂H₅ 1-1-276 CH₂═CHC₂H₄

— — —

C₃H₇ 1-1-277 C₃H₇CH═CH

— — —

CH₃ 1-1-278 CH₃CH═CHC₂H₄

— — —

C₂H₅ 1-1-279 C₂H₅

— — —

CH₂CH₂CHF₂ 1-1-280 CH₂FCH₂CH₂

— — —

C₄H₉ 1-1-281 CH₃

— — —

CH═CH₂ 1-1-282 C₄H₉

— — —

CH═CHCH₃ 1-1-283 C₂H₅

— — —

C₂H₄CH═CH₂ 1-1-284 C₃H₇

— — —

C₂H₄CH═CH₂ 1-1-285 C₃H₇

— — —

CH═CHC₃H₇

TABLE 20 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-286 C₂H₅

— — —

CH═CHC₃H₇ 1-1-287 C₅H₁₁

— — —

C₂H₄CH═CHCH₃ 1-1-288 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-1-289 CH₂═CH

— — —

C₂H₄CH═CH₂ 1-1-290 CH₃CH═CH

— — —

CH═CH₂ 1-1-291 C₂H₅OCH₂

— — —

C₃H₇ 1-1-292 C₃H₇

— — —

OC₂H₄CH═CH₂ 1-1-293 C₃H₇

CH₂CH₂ — —

C₂H₅ 1-1-294 C₂H₅

CH₂CH₂ — —

C₃H₇ 1-1-295 C₃H₇

CH₂O — —

C₂H₅ 1-1-296 C₂H₅

OCH₂ — —

C₃H₇ 1-1-297 C₄H₉

COO — —

C₄H₉ 1-1-298 C₃H₇

OCO — —

H 1-1-299 C₂H₅

CF₂O — —

C₇H₁₅ 1-1-300 CH₃

OCF₂ — —

C₂H₅

TABLE 21 (1-1)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-1-301 CH₃

— — —

C₅H₁₁ 1-1-302 CH₃

— — —

OC₂H₅ 1-1-303 CH₃

— — —

OC₂H₅ 1-1-304 CH₃

— — —

C₅H₁₁ 1-1-305 CH₃

— — —

C₂H₅ 1-1-306 C₂H₅

— — —

OC₄H₉ 1-1-307 C₂H₅

— — —

CH₃ 1-1-308 C₂H₅

— — —

C₂H₅ 1-1-309 C₂H₅

— — —

C₃H₇ 1-1-310 C₂H₅

— — —

C₄H₉ 1-1-311 C₃H₇

— — —

CH₃ 1-1-312 C₃H₇

— — —

CH═CH₂ 1-1-313 C₃H₇

— — —

CH═CHCH₃ 1-1-314 C₃H₇

— — —

CH═CHC₃H₇ 1-1-315 C₃H₇

— — —

C₂H₄CH═CH₂

TABLE 22 (1-1)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-1-316 C₄H₉

— — —

C₂H₄CH═CH₂ 1-1-317 C₄H₉

— — —

C₂H₄CH═CHCH₃ 1-1-318 C₄H₉

— — —

C₂H₄CH═CHCH₃ 1-1-319 C₄H₉

— — —

C₂H₄CH═CH₂ 1-1-320 C₄H₉

— — —

C₂H₄CH═CHCH₃ 1-1-321 C₅H₁₁

— — —

C₃H₇ 1-1-322 C₅H₁₁

— — —

OC₂H₄CH═CH₂ 1-1-323 C₅H₁₁

— — —

C₂H₅ 1-1-324 C₅H₁₁

— — —

C₃H₇ 1-1-325 C₅H₁₁

— — —

C₂H₅ 1-1-326 C₂H₅O

— — —

C₃H₇ 1-1-327 C₅H₁₁

— — —

C₄H₉ 1-1-328 C₂H₅O

— — —

C₇H₁₅ 1-1-329 C₃H₇

— — —

C₄H₉ 1-1-330 C₅H₁₁

— — —

C₂H₅

TABLE 23 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-331 C₃H₇

— — —

C₅H₁₁ 1-1-332 C₃H₇O

— — —

OC₂H₅ 1-1-333 C₅H₁₁

— — —

OC₂H₅ 1-1-334 C₂H₅O

— — —

C₅H₁₁ 1-1-335 C₄H₉

— — —

C₂H₅ 1-1-336 C₂H₅O

— — —

OC₄H₉ 1-1-337 CH₂═CH

— — —

CH₃ 1-1-338 CH₃CH═CH

— — —

C₂H₅ 1-1-339 CH₂═CHC₂H₄

— — —

C₃H₇ 1-1-340 C₃H₇CH═CH

— — —

C₄H₉ 1-1-341 CH₃CH═CHC₂H₄

— — —

CH₃ 1-1-342 C₄H₉

— — —

CH═CH₂ 1-1-343 C₂H₅

— — —

CH═CHCH₃ 1-1-344 C₃H₇

— — —

CH═CHC₃H₇ 1-1-345 C₃H₇

— — —

C₂H₄CH═CH₂

TABLE 24 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-346 C₂H₅

— — —

C₂H₄CH═CH₂ 1-1-347 C₅H₁₁

— — —

C₂H₄CH═CHCH₃ 1-1-348 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-1-349 CH₃CH═CHC₂H₄

— — —

C₂H₄CH═CH₂ 1-1-350 CH₂═CHC₂H₄

— — —

C₂H₄CH═CHCH₃ 1-1-351 C₄H₉OCH₂

— — —

C₃H₇ 1-1-352 C₃H₇

— — —

OC₂H₄CH═CH₂ 1-1-353 C₃H₇

CH₂CH₂ — —

C₂H₅ 1-1-354 C₂H₅

CH₂CH₂ — —

C₃H₇ 1-1-355 C₃H₇

CH₂O — —

C₂H₅ 1-1-356 C₂H₅

OCH₂ — —

C₃H₇ 1-1-357 C₄H₉O

COO — —

C₄H₉ 1-1-358 C₃H₇

OCO — —

C₇H₁₅ 1-1-359 C₂H₅

CF₂O — —

C₄H₉ 1-1-360 CH₃

OCF₂ — —

C₂H₅

TABLE 27 (1-1)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-1-361 C₃H₇

— — —

C₂H₅ 1-1-362 C₅H₁₁

— — —

C₄H₉ 1-1-363 CH₃

— — —

C₃H₇ 1-1-364 C₄H₉

— — —

C₂H₅ 1-1-365 CH₃

— — —

OC₂H₅ 1-1-366 C₂H₅

— — —

C₂H₅ 1-1-367 C₂H₅

— — —

C₃H₇ 1-1-368 C₂H₅

— — —

C₃H₇ 1-1-369 C₂H₅O

— — —

C₄H₉ 1-1-370 C₂H₅

— — —

C₅H₁₁ 1-1-371 C₃H₇

— — —

C₄H₉ 1-1-372 C₃H₇

(CH₂)₄ — —

C₂H₅ 1-1-373 C₂H₅

— — —

C₅H₁₁ 1-1-374 C₃H₇

— — —

C₄H₉ 1-1-375 C₃H₇

— — —

C₅H₁₁

TABLE 26 (1-1)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-1-376 C₄H₉

— — —

C₅H₁₁ 1-1-377 C₅H₁₁

— — —

C₂H₅ 1-1-378 C₄H₉

— — —

C₃H₇ 1-1-379 C₄H₉

CH═CH — —

C₄H₉ 1-1-380 C₃H₇

— — —

C₅H₁₁ 1-1-381 C₅H₁₁

— — —

OC₄H₉ 1-1-382 C₅H₁₁

— — —

C₂H₅ 1-1-383 C₅H₁₁

— — —

C₃H₇ 1-1-384 C₅H₁₁

— — —

C₄H₉ 1-1-385 C₂H₅O

— — —

C₅H₁₁ 1-1-386 C₂H₅O

C≡C — —

C₄H₉ 1-1-387 C₅H₁₁

— — —

OC₂H₅ 1-1-388 C₂H₅O

— — —

C₅H₁₁ 1-1-389 C₅H₁₁

— — —

C₃H₇ 1-1-390 C₃H₇

— — —

C₅H₁₁

TABLE 27 (1-1)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-1-391 C₃H₇

—

—

C₅H₁₁ 1-1-392 C₅H₁₁

—

—

C₃H₇ 1-1-393 C₃H₇

—

—

C₅H₁₁ 1-1-394 C₅H₁₁

—

—

C₃H₇ 1-1-395 C₃H₇

—

—

C₅H₁₁ 1-1-396 C₅H₁₁

—

—

C₃H₇ 1-1-397 C₃H₇

—

—

C₅H₁₁ 1-1-398 C₅H₁₁

—

—

C₃H₇ 1-1-399 C₃H₇

—

—

C₅H₁₁ 1-1-400 C₅H₁₁

CH₂CH₂

—

C₃H₇ 1-1-401 C₃H₇

CH₂CH₂

—

C₅H₁₁ 1-1-402 C₅H₁₁

—

CH₂CH₂

C₃H₇ 1-1-403 C₃H₇

—

CH₂CH₂

C₅H₁₁ 1-1-404 C₅H₁₁

—

—

C₃H₇ 1-1-405 C₃H₇

—

—

C₅H₁₁

TABLE 28 (1-1)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-1-406 C₅H₁₁

—

—

C₃H₇ 1-1-407 C₃H₇

—

—

C₅H₁₁ 1-1-408 C₃H₇

—

—

C₅H₁₁ 1-1-409 C₃H₇

—

—

C₅H₁₁ 1-1-410 C₃H₇

—

—

C₅H₁₁

TABLE 29 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-1 CH₃ — —

—

CH₃ 2-1-2 CH₃ — —

—

C₂H₅ 2-1-3 CH₃ — —

—

C₃H₇ 2-1-4 CH₃ — —

—

C₄H₉ 2-1-5 CH₃ — —

—

C₅H₁₁ 2-1-6 C₂H₅ — —

—

CH₃ 2-1-7 C₂H₅ — —

—

C₂H₅ 2-1-8 C₂H₅ — —

—

C₃H₇ 2-1-9 C₂H₅ — —

—

C₄H₉ 2-1-10 C₂H₅ — —

—

C₅H₁₁ 2-1-11 C₃H₇ — —

—

CH₃ 2-1-12 C₃H₇ — —

—

C₂H₅ 2-1-13 C₃H₇ — —

—

C₃H₇ 2-1-14 C₃H₇ — —

—

C₄H₉ 2-1-15 C₃H₇ — —

—

C₅H₁₁

TABLE 30 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-16 C₄H₉ — —

—

CH₃ 2-1-17 C₄H₉ — —

—

C₂H₅ 2-1-18 C₄H₉ — —

—

C₃H₇ 2-1-19 C₄H₉ — —

—

C₄H₉ 2-1-20 C₄H₉ — —

—

C₅H₁₁ 2-1-21 C₅H₁₁ — —

—

CH₃ 2-1-22 C₅H₁₁ — —

—

C₂H₅ 2-1-23 C₅H₁₁ — —

—

C₃H₇ Cr 77.0 SmB 133.2 SmA 167.7 N 246.2 Iso T_(NI): 268.6° C., Δ ε:−6.9, Δ n: 0.141 2-1-24 C₅H₁₁ — —

—

C₄H₉ 2-1-25 C₅H₁₁ — —

—

C₅H₁₁ 2-1-26 C₂H₅O — —

—

C₄H₉ 2-1-27 C₅H₁₁ — —

—

OC₂H₅ 2-1-28 C₂H₅O — —

—

OC₄H₉ 2-1-29 CH₂═CH — —

—

C₃H₇ Cr1 69.9 Cr2 80.8 SmB 96.3 SmA 123.1 N 252.6 Iso T_(NI): 215.9° C.,Δ ε: −5.2, Δ n: 0.114 2-1-30 CH₂═CH — —

—

C₅H₁₁

Table 31 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-31 CH₃CH═CH — —

—

C₃H₇ 2-1-32 CH₃CH═CH — —

—

C₅H₁₁ 2-1-33 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-1-34 CH₂═CHC₂H₄ — —

—

C₅H₁₁ 2-1-35 C₃H₇CH═CH — —

—

C₂H₅ 2-1-36 C₃H₇CH═CH — —

—

C₃H₇ 2-1-37 CH₃CH═CHC₂H₄ — —

—

CH₃ 2-1-38 CH₃CH═CHC₂H₄ — —

—

C₂H₅ 2-1-39 C₃H₇ — —

—

CH═CH₂ 2-1-40 C₅H₁₁ — —

—

CH═CH₂ 2-1-41 C₃H₇ — —

—

CH═CHCH₃ 2-1-42 C₄H₉ — —

—

CH═CHCH₃ 2-1-43 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-1-44 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-1-45 CH₃ — —

—

CH═CHC₃H₇

TABLE 32 (2-1)

No. Ra A^(l) Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-46 C₂H₅ — —

—

CH═CHC₃H₇ 2-1-47 C₂H₅ — —

—

C₂H₄CH═CHCH₃ 2-1-48 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-1-49 CH₂═CH — —

—

C₂H₄CH═CH₂ 2-1-50 CH₃CH═CH — —

—

CH═CH₂ 2-1-51 C₃H₇OCH₂ — —

—

C₃H₇ 2-1-52 C₅H₁₁ — —

—

OC₂H₄CH═CH₂ 2-1-53 C₃H₇ — —

CH₂CH₂

C₂H₅ 2-1-54 C₅H₁₁ — —

CH₂CH₂

C₃H₇ 2-1-55 C₃H₇ — —

CH₂O

C₂H₅ 2-1-56 C₅H₁₁ — —

OCH₂

C₃H₇ 2-1-57 H — —

COO

C₄H₉ 2-1-58 C₇H₁₅ — —

OCO

C₄H₉ 2-1-59 C₂H₅ — —

CF₂O

C₆H₁₃ 2-1-60 CH₃ — —

OCF₂

C₂H₅

TABLE 33 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-61 CH₃ — —

—

CH₃ 2-1-62 CH₃ — —

—

C₂H₅ 2-1-63 CH₃ — —

—

C₃H₇ 2-1-64 CH₃ — —

—

C₄H₉ 2-1-65 CH₃ — —

—

C₅H₁₁ 2-1-66 C₂H₅ — —

—

CH₃ 2-1-67 C₂H₅ — —

—

C₂H₅ 2-1-68 C₂H₅ — —

—

C₃H₇ 2-1-69 C₂H₅ — —

—

C₄H₉ 2-1-70 C₂H₅ — —

—

C₅H₁₁ 2-1-71 C₃H₇ — —

—

CH₃ 2-1-72 C₃H₇ — —

—

C₂H₅ 2-1-73 C₃H₇ — —

—

C₃H₇ 2-1-74 C₃H₇ — —

—

C₄H₉ 2-1-75 C₃H₇ — —

—

C₅H₁₁

TABLE 34 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-76 C₄H₉ — —

—

CH₃ 2-1-77 C₄H₉ — —

—

C₂H₅ 2-1-78 C₄H₉ — —

—

C₃H₇ 2-1-79 C₄H₉ — —

—

C₄H₉ 2-1-80 C₄H₉ — —

—

C₅H₁₁ 2-1-81 C₅H₁₁ — —

—

CH₃ 2-1-82 C₅H₁₁ — —

—

C₂H₅ 2-1-83 C₅H₁₁ — —

—

C₃H₇ 2-1-84 C₅H₁₁ — —

—

C₄H₉ 2-1-85 C₅H₁₁ — —

—

C₃H₇ Cr (50.7 SmX) 76.6 SmC 80.9 N 239.5 Iso T_(NI): 218.6° C., Δ ε:−5.0, Δ n: 0.167 2-1-86 C₂H₅O — —

—

C₄H₉ 2-1-87 C₅H₁₁ — —

—

OC₂H₅ 2-1-88 C₂H₅O — —

—

OC₄H₉ 2-1-89 C₅H₁₁ — —

—

C₃H₇ 2-1-90 C₃H₇ — —

—

C₅H₁₁

TABLE 35 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-91 C₂H₅ — —

—

C₄H₉ 2-1-92 C₅H₁₁ — —

—

C₂H₅ 2-1-93 CH₂═CH — —

—

C₃H₇ 2-1-94 CH₂═CH — —

—

C₅H₁₁ 2-1-95 CH₃CH═CH — —

—

C₂H₅ 2-1-96 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-1-97 C₃H₇CH═CH — —

—

CH₃ 2-1-98 CH₃CH═CHC₂H₄ — —

—

C₂H₅ 2-1-99 C₃H₇ — —

—

CH═CH₂ 2-1-100 C₅H₁₁ — —

—

CH═CH₂ 2-1-101 C₃H₇ — —

—

CH═CHCH₃ 2-1-102 C₄H₉ — —

—

CH═CHCH₃ 2-1-103 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-1-104 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-1-105 CH₃ — —

—

CH═CHC₃H₇

TABLE 36 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-106 C₂H₅ — —

—

CH═CHC₃H₇ 2-1-107 C₂H₅ — —

—

C₂H₄CH═CHCH₃ 2-1-108 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-1-109 CH₂═CH — —

—

C₂H₄CH═CH₂ 2-1-110 CH₃CH═CH — —

—

CH═CH₂ 2-1-111 C₅H₁₁OCH₂ — —

—

C₃H₇ 2-1-112 C₃H₇ — —

—

OC₂H₄CH═CH₂ 2-1-113 C₄H₉ — —

CH₂CH₂

C₂H₅ 2-1-114 C₅H₁₁ — —

CH₂CH₂

C₃H₇ 2-1-115 C₃H₇ — —

CH₂O

C₂H₅ 2-1-116 C₅H₁₁ — —

OCH₂

C₆H₁₃ 2-1-117 C₅H₁₁ — —

COO

C₄H₉ 2-1-118 C₂H₅ — —

OCO

C₄H₉ 2-1-119 C₂H₅ — —

CF₂O

CH₃ 2-1-120 C₄H₉ — —

OCF₂

C₂H₅

TABLE 37 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-121 CH₃ — —

—

CH₃ 2-1-122 CH₃ — —

—

C₂H₅ 2-1-123 CH₃ — —

—

C₃H₇ 2-1-124 CH₃ — —

—

C₄H₉ 2-1-125 CH₃ — —

—

C₅H₁₁ 2-1-126 C₂H₅ — —

—

CH₃ 2-1-127 C₂H₅ — —

—

C₂H₅ 2-1-128 C₂H₅ — —

—

C₃H₇ 2-1-129 C₂H₅ — —

—

C₄H₉ 2-1-130 C₂H₅ — —

—

C₅H₁₁ 2-1-131 C₃H₇ — —

—

CH₃ 2-1-132 C₃H₇ — —

—

C₂H₅ 2-1-133 C₃H₇ — —

—

C₃H₇ 2-1-134 C₃H₇ — —

—

C₄H₉ 2-1-135 C₃H₇ — —

—

C₅H₁₁

TABLE 38 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-136 C₄H₉ — —

—

CH₃ 2-1-137 C₄H₉ — —

—

C₂H₅ 2-1-138 C₄H₉ — —

—

C₃H₇ 2-1-139 C₄H₉ — —

—

C₄H₉ 2-1-140 C₄H₉ — —

—

C₅H₁₁ 2-1-141 C₅H₁₁ — —

—

CH₃ 2-1-142 C₅H₁₁ — —

—

C₂H₅ 2-1-143 C₅H₁₁ — —

—

C₃H₇ Cr 112.0 N 252.4 Iso T_(NI): 232.6° C., Δ ε: −4.3, Δ n: 0.2472-1-144 C₅H₁₁ — —

—

C₄H₉ 2-1-145 C₅H₁₁ — —

—

C₅H₁₁ 2-1-146 C₂H₅O — —

—

C₄H₉ 2-1-147 C₅H₁₁ — —

—

OC₂H₅ 2-1-148 C₂H₅O — —

—

OC₄H₉ 2-1-149 C₃H₇ — —

—

OC₄H₉ 2-1-150 C₅H₁₁ — —

—

OC₂H₅

TABLE 39 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-151 C₃H₇ — —

—

C₅H₁₁ 2-1-152 C₃H₇O — —

—

C₅H₁₁ 2-1-153 C₅H₁₁ — —

—

OC₂H₅ 2-1-154 CH₂═CH — —

—

C₅H₁₁ 2-1-155 CH₃CH═CH — —

—

C₂H₅ 2-1-156 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-1-157 C₃H₇CH═CH — —

—

CH₃ 2-1-158 CH₃CH═CHC₂H₄ — —

—

C₂H₅ 2-1-159 C₂H₅ — —

—

CH₂CH₂CHF₂ 2-1-160 CH₂FCH₂CH₂ — —

—

C₄H₉ 2-1-161 CH₃ — —

—

CH═CH₂ 2-1-162 C₄H₉ — —

—

CH═CHCH₃ 2-1-163 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-1-164 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-1-165 C₃H₇ — —

—

CH═CHC₃H₇

TABLE 40 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-166 C₂H₅ — —

—

CH═CHC₃H₇ 2-1-167 C₅H₁₁ — —

—

C₂H₄CH═CHCH₃ 2-1-168 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-1-169 CH₂═CH — —

—

C₂H₄CH═CH₂ 2-1-170 CH₃CH═CH — —

—

CH═CH₂ 2-1-171 C₂H₅OCH₂ — —

—

C₃H₇ 2-1-172 C₃H₇ — —

—

OC₂H₄CH═CH₂ 2-1-173 C₃H₇ — —

CH₂CH₂

C₂H₅ 2-1-174 C₂H₅ — —

C≡C

C₃H₇ 2-1-175 C₃H₇ — —

CH₂O

C₂H₅ 2-1-176 C₂H₅ — —

OCH₂

C₃H₇ 2-1-177 C₄H₉ — —

COO

C₄H₉ 2-1-178 C₃H₇ — —

OCO

H 2-1-179 C₂H₅ — —

CF₂O

C₇H₁₅ 2-1-180 CH₃ — —

OCF₂

C₂H₅

TABLE 41 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-181 CH₃ — —

—

CH₃ 2-1-182 CH₃ — —

—

C₂H₅ 2-1-183 CH₃ — —

—

C₃H₇ 2-1-184 CH₃ — —

—

C₄H₉ 2-1-185 CH₃ — —

—

C₅H₁₁ 2-1-186 C₂H₅ — —

—

CH₃ 2-1-187 C₂H₅ — —

—

C₂H₅ 2-1-188 C₂H₅ — —

—

C₃H₇ 2-1-189 C₂H₅ — —

—

C₄H₉ 2-1-190 C₂H₅ — —

—

C₅H₁₁ 2-1-191 C₃H₇ — —

—

CH₃ 2-1-192 C₃H₇ — —

—

C₂H₅ 2-1-193 C₃H₇ — —

—

C₃H₇ 2-1-194 C₃H₇ — —

—

C₄H₉ 2-1-195 C₃H₇ — —

—

C₅H₁₁

TABLE 42 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-196 C₄H₉ — —

—

CH₃ 2-1-197 C₄H₉ — —

—

C₂H₅ 2-1-198 C₄H₉ — —

—

C₃H₇ 2-1-199 C₄H₉ — —

—

C₄H₉ 2-1-200 C₄H₉ — —

—

C₅H₁₁ 2-1-201 C₅H₁₁ — —

—

CH₃ 2-1-202 C₅H₁₁ — —

—

C₂H₅ 2-1-203 C₅H₁₁ — —

—

C₃H₇ 2-1-204 C₅H₁₁ — —

—

C₄H₉ 2-1-205 C₅H₁₁ — —

—

C₃H₇ 2-1-206 C₂H₅O — —

—

C₄H₉ 2-1-207 C₅H₁₁ — —

—

OC₂H₅ 2-1-208 C₂H₅O — —

—

OC₄H₉ 2-1-209 C₅H₁₁ — —

—

C₃H₇ 2-1-210 C₃H₇ — —

—

C₅H₁₁

TABLE 43 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-211 C₂H₅ — —

—

CH₂CH₂F 2-1-212 CH₃OC₂H₄ — —

—

C₂H₅ 2-1-213 CH₂═CH — —

—

C₃H₇ 2-1-214 CH₂═CH — —

—

C₅H₁₁ 2-1-215 CH₃CH═CH — —

—

C₂H₅ 2-1-216 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-1-217 C₃H₇CH═CH — —

—

C₄H₉ 2-1-218 CH₃CH═CHC₂H₄ — —

—

C₂H₅ 2-1-219 C₃H₇ — —

—

CH═CH₂ 2-1-220 C₅H₁₁ — —

—

CH═CH₂ 2-1-221 C₃H₇ — —

—

CH═CHCH₃ 2-1-222 C₄H₉ — —

—

CH═CHCH₃ 2-1-223 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-1-224 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-1-225 C₄H₉ — —

—

CH═CHC₃H₇

TABLE 44 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-226 C₂H₅ — —

—

CH═CHC₃H₇ 2-1-227 C₂H₅ — —

—

C₂H₄CH═CHCH₃ 2-1-228 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-1-229 CH₂═CH — —

—

CH═CH₂ 2-1-230 CH₃CH═CH — —

—

C₂H₄CH═CH₂ 2-1-231 CH₃OCH₂ — —

—

C₃H₇ 2-1-232 C₂H₅ — —

—

OC₂H₄CH═CH₂ 2-1-233 C₅H₁₁ — —

CH₂CH₂

C₂H₅ 2-1-234 C₅H₁₁ — —

CH₂CH₂

C₃H₇ 2-1-235 C₂H₅ — —

CH₂O

C₃H₇ 2-1-236 C₃H₇ — —

OCH₂

CH₃ 2-1-237 C₅H₁₁ — —

COO

C₄H₉ 2-1-238 C₂H₅ — —

OCO

C₃H₇ 2-1-239 C₂H₅ — —

CF₂O

C₆H₁₃ 2-1-240 C₄H₉ — —

OCF₂

C₂H₅

TABLE 45 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-241 CH₃ — —

—

CH₃ 2-1-242 CH₃ — —

—

C₂H₅ 2-1-243 CH₃ — —

—

C₃H₇ 2-1-244 CH₃ — —

—

C₄H₉ 2-1-245 CH₃ — —

—

C₅H₁₁ 2-1-246 C₂H₅ — —

—

CH₃ 2-1-247 C₂H₅ — —

—

C₂H₅ 2-1-248 C₂H₅ — —

—

C₃H₇ 2-1-249 C₂H₅ — —

—

C₄H₉ 2-1-250 C₂H₅ — —

—

C₅H₁₁ 2-1-251 C₃H₇ — —

—

CH₃ 2-1-252 C₃H₇ — —

—

C₂H₅ 2-1-253 C₃H₇ — —

—

C₃H₇ 2-1-254 C₃H₇ — —

—

C₄H₉ 2-1-255 C₃H₇ — —

—

C₅H₁₁

TABLE 46 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-256 C₄H₉ — —

—

CH₃ 2-1-257 C₄H₉ — —

—

C₂H₅ 2-1-258 C₄H₉ — —

—

C₃H₇ 2-1-259 C₄H₉ — —

—

C₄H₉ 2-1-260 C₄H₉ — —

—

C₅H₁₁ 2-1-261 C₅H₁₁ — —

—

CH₃ 2-1-262 C₅H₁₁ — —

—

C₂H₅ 2-1-263 C₅H₁₁ — —

—

C₃H₇ 2-1-264 C₅H₁₁ — —

—

C₄H₉ 2-1-265 C₅H₁₁ — —

—

C₅H₁₁ 2-1-266 C₂H₅O — —

—

C₄H₉ 2-1-267 C₅H₁₁ — —

—

OC₂H₅ 2-1-268 C₂H₅O — —

—

OC₄H₉ 2-1-269 C₃H₇ — —

—

OC₄H₉ 2-1-270 C₅H₁₁ — —

—

OC₂H₅

TABLE 47 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-271 C₃H₇ — —

—

C₅H₁₁ 2-1-272 C₅H₁₁ — —

—

C₂H₅ 2-1-273 C₄H₉O — —

—

C₃H₇ 2-1-274 CH₂═CH — —

—

C₅H₁₁ 2-1-275 CH₃CH═CH — —

—

C₂H₅ 2-1-276 C₃H₇CH═CH — —

—

C₃H₇ 2-1-277 CH₂═CHC₂H₄ — —

—

CH₃ 2-1-278 CH₂═CHC₂H₄ — —

—

C₂H₅ 2-1-279 CH₃CH═CHC₂H₄ — —

—

C₃H₇ 2-1-280 CH₃CH═CHC₂H₄ — —

—

C₄H₉ 2-1-281 C₃H₇ — —

—

CH₂OC₃H₇ 2-1-282 C₄H₉ — —

—

CH₂CH₂F 2-1-283 C₂H₅ — —

—

CH═CH₂ 2-1-284 C₃H₇ — —

—

CH═CHCH₃ 2-1-285 C₃H₇ — —

—

CH═CHC₃H₇

TABLE 48 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-286 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-1-287 C₅H₁₁ — —

—

C₂H₄CH═CH₂ 2-1-288 C₄H₉ — —

—

C₂H₄CH═CHCH₃ 2-1-289 CH₂═CHC₂H₄ — —

—

CH═CH₂ 2-1-290 CH₃CH═CHC₂H₄ — —

—

CH═CHCH₃ 2-1-291 CH₃OCH₂CH₂ — —

—

C₃H₇ 2-1-292 C₃H₇ — —

—

OC₂H₄CH═CH₂ 2-1-293 C₅H₁₁ — —

CH₂CH₂

C₂H₅ 2-1-294 C₅H₁₁ — —

CH₂CH₂

C₃H₇ 2-1-295 C₃H₇ — —

CH₂O

C₅H₁₁ 2-1-296 C₂H₅ — —

OCH₂

C₃H₇ 2-1-297 C₄H₉ — —

COO

C₄H₉ 2-1-298 C₃H₇ — —

OCO

C₂H₅ 2-1-299 C₁₀H₂₁ — —

CF₂O

C₂H₅ 2-1-300 CH₃ — —

OCF₂

CH₃

TABLE 49 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-301 CH₃ — —

—

CH₃ 2-1-302 CH₃ — —

—

C₂H₅ 2-1-303 CH₃ — —

—

C₃H₇ 2-1-304 CH₃ — —

—

C₄H₉ 2-1-305 CH₃ — —

—

C₅H₁₁ 2-1-306 C₂H₅ — —

—

CH₃ 2-1-307 C₂H₅ — —

—

C₂H₅ 2-1-308 C₂H₅ — —

—

C₃H₇ 2-1-309 C₂H₅ — —

—

C₄H₉ 2-1-310 C₂H₅ — —

—

C₅H₁₁ 2-1-311 C₃H₇ — —

—

CH₃ 2-1-312 C₃H₇ — —

—

C₂H₅ 2-1-313 C₃H₇ — —

—

C₃H₇ 2-1-314 C₃H₇ — —

—

C₄H₉ 2-1-315 C₃H₇ — —

—

C₅H₁₁

TABLE 50 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-316 C₄H₉ — —

—

CH₃ 2-1-317 C₄H₉ — —

—

C₂H₅ 2-1-318 C₄H₉ — —

—

C₃H₇ 2-1-319 C₄H₉ — —

—

C₄H₉ 2-1-320 C₄H₉ — —

—

C₅H₁₁ 2-1-321 C₅H₁₁ — —

—

CH₃ 2-1-322 C₅H₁₁ — —

—

C₂H₅ 2-1-323 C₅H₁₁ — —

—

C₃H₇ 2-1-324 C₅H₁₁ — —

—

C₄H₉ 2-1-325 C₅H₁₁ — —

—

C₅H₁₁ 2-1-326 C₂H₅O — —

—

C₄H₉ 2-1-327 C₅H₁₁ — —

—

OC₂H₅ 2-1-328 C₂H₅O — —

—

OC₄H₉ 2-1-329 C₃H₇ — —

—

OC₄H₉ 2-1-330 C₅H₁₁ — —

—

OC₂H₅

TABLE 51 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-331 C₃H₇ — —

—

C₅H₁₁ 2-1-332 C₃H₇O — —

—

OC₂H₅ 2-1-333 C₅H₁₁ — —

—

OC₂H₅ 2-1-334 C₂H₅O — —

—

C₅H₁₁ 2-1-335 C₄H₉ — —

—

C₂H₅ 2-1-336 C₂H₅O — —

—

OC₄H₉ 2-1-337 CH₂═CH — —

—

CH₃ 2-1-338 CH₃CH═CH — —

—

C₂H₅ 2-1-339 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-1-340 C₃H₇CH═CH — —

—

C₄H₉ 2-1-341 CH₃CH═CHC₂H₄ — —

—

CH₃ 2-1-342 C₄H₉ — —

—

CH═CH₂ 2-1-343 C₂H₅ — —

—

CH═CHCH₃ 2-1-344 C₃H₇ — —

—

CH═CHC₃H₇ 2-1-345 C₃H₇ — —

—

C₂H₄CH═CH₂

TABLE 52 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-346 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-1-347 C₅H₁₁ — —

—

C₂H₄CH═CHCH₃ 2-1-348 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-1-349 CH₃CH═CHC₂H₄ — —

—

C₂H₄CH═CH₂ 2-1-350 CH₂═CHC₂H₄ — —

—

C₂H₄CH═CHCH₃ 2-1-351 C₄H₉OCH₂ — —

—

C₃H₇ 2-1-352 C₃H₇ — —

—

OC₂H₄CH═CH₂ 2-1-353 C₃H₇ — —

CH₂CH₂

C₂H₅ 2-1-354 C₂H₅ — —

CH₂CH₂

C₃H₇ 2-1-355 C₃H₇ — —

CH₂O

C₂H₅ 2-1-356 C₂H₅ — —

OCH₂

C₃H₇ 2-1-357 C₄H₉O — —

COO

C₄H₉ 2-1-358 C₃H₇ — —

OCO

C₇H₁₅ 2-1-359 C₂H₅ — —

CF₂O

C₄H₉ 2-1-360 CH₃ — —

OCF₂

C₂H₅

TABLE 53 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-361 C₃H₇ — —

—

C₅H₁₁ 2-1-362 C₅H₁₁ — —

—

C₂H₅ 2-1-363 CH₃ — —

—

C₃H₇ 2-1-364 C₄H₉ — —

—

C₂H₅ 2-1-365 C₅H₁₁ — —

—

OC₄H₉ 2-1-366 CH₃ — —

CH═CH

C₂H₅ 2-1-367 C₂H₅ — —

—

C₃H₇ 2-1-368 C₂H₅ — —

—

C₃H₇ 2-1-369 C₃H₇O — —

—

C₄H₉ 2-1-370 C₂H₅ — —

—

C₅H₁₁ 2-1-371 C₃H₇ — —

—

C₄H₉ 2-1-372 C₃H₇ — —

—

C₂H₅ 2-1-373 C₂H₅ — —

—

C₅H₁₁ 2-1-374 C₃H₇ — —

—

C₄H₉ 2-1-375 C₃H₇ — —

—

C₅H₁₁

TABLE 54 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-376 C₄H₉ — —

—

C₅H₁₁ 2-1-377 C₅H₁₁ — —

—

C₂H₅ 2-1-378 C₄H₉ — —

—

C₃H₇ 2-1-379 C₄H₉ — —

—

C₄H₉ 2-1-380 C₄H₉ — —

—

C₅H₁₁ 2-1-381 C₅H₁₁ — —

—

OC₄H₉ 2-1-382 C₅H₁₁ — —

—

C₂H₅ 2-1-383 C₅H₁₁ — —

—

C₃H₇ 2-1-384 C₅H₁₁ — —

—

C₄H₉ 2-1-385 CH₃O — —

—

C₅H₁₁ 2-1-386 C₂H₅O — —

—

C₄H₉ 2-1-387 C₅H₁₁ — —

(CH₂)₄

CH₃ 2-1-388 C₄H₉O — —

—

C₅H₁₁ 2-1-389 C₅H₁₁ — —

—

C₃H₇ 2-1-390 C₃H₇ — —

—

C₅H₁₁

TABLE 55

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-391 C₃H₇

—

—

C₅H₁₁ 2-1-392 C₅H₁₁

—

—

C₃H₇ 2-1-393 C₃H₇

—

—

C₅H₁₁ 2-1-394 C₅H₁₁

—

—

C₃H₇ 2-1-395 C₃H₇

—

—

C₅H₁₁ 2-1-396 C₅H₁₁

—

—

C₃H₇ 2-1-397 C₃H₇

—

—

C₅H₁₁ 2-1-398 C₃H₇

—

—

C₂H₅ 2-1-399 C₃H₇

—

—

C₅H₁₁ 2-1-400 C₅H₁₁

CH₂CH₂

—

C₃H₇ 2-1-401 C₃H₇

CH₂CH₂

—

C₅H₁₁ 2-1-402 C₅H₁₁

—

CH₂CH₂

C₃H₇ 2-1-403 C₃H₇

—

CH₂CH₂

C₅H₁₁ 2-1-404 C₅H₁₁

—

—

C₃H₇ 2-1-405 C₃H₇

—

—

C₅H₁₁

TABLE 56 (2-1)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-1-406 C₅H₁₁

—

—

C₃H₇ 2-1-407 C₃H₇

—

—

C₅H₁₁ 2-1-408 C₃H₇

—

—

C₅H₁₁ 2-1-409 C₃H₇

—

—

C₅H₁₁ 2-1-410 C₃H₇

—

—

C₅H₁₁

Example 9 Synthesis of 4-(4-pentylcyclohexyl)benzoic acid2,3-difluoro-4′-propylbiphenyl-4-ylester (No. 1-2-263)

Under a nitrogen atmosphere, 4-(4-trans-4-pentylcyclohexyl benzoic acid(13) (3.3 g), 2,3-difluoro-4′-propylbiphenyl-4-ol (14) (3.0 g),1,3-dicyclocarbodiimide (DCC) (2.6 g), and 4-dimethylaminopyridine(DMAP) (0.15 g) were put in methylene chloride (CH₂Cl₂) (30 ml), andstirred at 25° C. for another 20 hours. After completion of the reactionhad been confirmed by means of gas chromatographic analysis, methylenechloride (20 ml) and water (50 ml) were added, and mixed. Then, themixture was allowed to stand until it had separated into an organicphase and an aqueous phase, and an extractive operation into an organicphase was carried out. The organic phase obtained was fractionated,washed with water, and dried over anhydrous magnesium sulfate. Theresidue obtained was purified with a fractional operation by means ofcolumn chromatography using toluene as the eluent and silica gel as thestationary phase powder. The residue obtained was further purified byrecrystallization from a mixed solvent of heptane and THF (volume ratio;heptane:THF=2:1), and dried, giving 4.6 g of4-(trans-4-pentylcyclohexyl)benzoic acid2,3-difluoro-4′-propylbiphenyl-4-ylester (No. 1-2-263). The yield basedon the compound (13) was 75.1%.

The compound (14) can be synthesized according to a procedure similar tothat for 3-chloro-2-fluoro-4′-propylbiphenyl-4-ol, which is described inWO 2006/093189 A, by use of 1-bromo-2,3-difluoro-4-methoxybenzene as astarting material.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified as 4-(trans-4-pentylcyclohexyl)benzoicacid 2,3-difluoro-4′-propylbiphenyl-4-ylester. The measurement solventwas CDCl₃.

Chemical shift δ (ppm); 8.14(d, 2H), 7.46(d, 2H), 7.36(d, 2H), 7.27(d,2H), 7.21(t, 1H), 7.08(t, 1H), 2.64(t, 2H), 2.57(tt, 1H), 1.93-1.89(t,4H), 1.73-1.65(m, 2H), 1.49(qt, 2H), 1.37-1.22(m, 9H), 1.07(qt, 2H),0.98(t, 3H), and 0.90(t, 3H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-2-263) were as follows.

Transition temperature: Cr 122.5 N 289.8 Iso.

T_(NI)=232.6° C., Δε=−2.0, Δn=0.219.

Example 10 Synthesis of trans-4-pentylcyclohexanecarboxylic acid2,3-difluoro-4-(trans-4′-propylbicyclohexyl-trans-4-yl)phenylester (No.2-2-23)

Under a nitrogen atmosphere, trans-4-pentylcyclohexyl carboxylic acid(15) (2.2 g), the compound (10) (3.7 g), 1,3-dicyclocarbodiimide (2.3g), and 4-dimethylaminopyridine (0.14 g) were put in methylene chloride(CH₂Cl₂) (30 ml), and stirred at 25° C. for another 4 hours. Aftercompletion of the reaction had been confirmed by means of gaschromatographic analysis, methylene chloride (20 ml) and water (50 ml)were added, and mixed. Then, the mixture was allowed to stand until ithad separated into an organic phase and an aqueous phase, and anextractive operation into an organic phase was carried out. The organicphase obtained was fractionated, washed with water, and dried overanhydrous magnesium sulfate. The solution obtained was concentratedunder reduced pressure, and the residue was purified with a fractionaloperation by means of column chromatography using toluene as the eluentand silica gel as the stationary phase powder. The residue obtained wasfurther purified by recrystallization from a mixed solvent of heptaneand THF (volume ratio; heptane:THF=2:1), and dried, giving 3.4 g oftrans-4-pentylcyclohexanecarboxylic acid2,3-difluoro-4-(trans-4′-propylbicyclohexyl-trans-4-yl)phenylester (No.2-2-23). The yield based on the compound (15) was 58.8%.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified astrans-4-pentylcyclohexanecarboxylicacid2,3-difluoro-4-(trans-4′-propylbicyclohexyl-trans-4-yl)phenylester. Themeasurement solvent was CDCl₃.

Chemical shift δ (ppm); 6.93(t, 1H), 6.80(t, 1H), 2.78(tt, 1H), 2.52(tt,1H), 2.14(d, 2H), 1.89-1.83(m, 6H), 1.77-1.72(m, 4H), 1.58-1.52(m, 2H),1.46-1.39(m, 2H), 1.35-0.93(m, 22H), and 0.90-0.84(m, 8H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 2-2-23) were as follows.

Transition temperature: Cr 84.5 SmA 187.8 N 310.3 Iso.

T_(NI)=251.9° C., Δε=−3.2, Δn=0.114.

Example 11 Synthesis of 4-(trans-4-propylcyclohexyl)benzoic acid4′-(trans-4-ethylcyclohexyl)-2,3-difluorobiphenyl-4-yl ester(No.2-2-398)

4-(trans-4-Propylcyclohexyl)benzoic acid4′-(trans-4-ethylcyclohexyl)-2,3-difluorobiphenyl-4-yl ester (No.2-2-398) can be synthesized by selecting 4-(trans-4-propylcyclohexyl)benzoic acid (16) as benzoic acid and4′-(trans-4-ethylcyclohexyl)-2,3-difluorobiphenyl-4-ol (17) as a phenolderivative, and applying a similar technique as that shown in Example 7or 9.

Example 12

A variety of compounds were synthesized according to the procedure shownin Examples 9, 10, and 11, using corresponding starting materials, andthe compounds were confirmed to be objective.trans-4′-Pentylbicyclohexyl-trans-4-carboxylic acid2,3-difluoro-4-(trans-4-propylcyclohexyl)phenylester (No. 1-2-23)

Chemical shift δ (ppm); 6.93(t, 1H), 6.80(t, 1H), 2.80(tt, 1H), 2.50(tt,1H), 2.16(d, 2H), 1.86-1.70(m, 10H), 1.58-1.41(m, 4H), 1.38-0.94(m,22H), and 0.91-0.81(m, 8H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-2-23) were as follows.

Transition temperature: Cr 55.2 SmC 74.9 SmA 179.6 N 307.2 Iso.

T_(NI)=255.9° C., Δε=−3.6, Δn=0.114.

trans-4′-Pentylbicyclohexyl-trans-4-carboxylic acid2,3-difluoro-4-(trans-4-ethoxycyclohexyl)phenylester (No. 1-2-27)

Chemical shift delta (ppm); 6.92(t, 1H), 6.81(t, 1H), 3.55(q, 2H),3.29(tt, 1H), 2.81(tt, 1H), 2.50(tt, 1H), 2.16(d, 4H), 1.95-1.82(m, 4H),1.80-1.68(m, 4H), 1.59-1.44(m, 4H), 1.43-0.92(m, 20H), and 0.91-0.80(m,5H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-2-27) were as follows.

Transition temperature: Cr 57.0 SmB 161.9 SmC 174.4 N 300.8 Iso.

T_(NI)=239.3° C., Δε=−3.9, Δn=0.109.

trans-4′-Pentylcyclohexyl-trans 4-carboxylic acid2,3-difluoro-4-(trans-4-propylcyclohexyl)phenylester (No. 1-2-83)

Chemical shift δ (ppm); 8.12(d, 2H), 7.35(d, 2H), 7.01-6.93(m, 2H),2.84(tt, 1H) and 2.57(tt, 1H), 1.92-1.87(m, 8H), 1.53-1.44(m, 4H),1.39-1.20(m, 14H), 1.13-1.03(m, 4H), and 0.92-0.89(m, 6H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-2-83) were as follows.

Transition temperature: Cr₁ 65.5 Cr₂ 113.0 N 297.9 Iso.

T_(NI)=243.9° C., Δε=−2.8, Δn=0.154.

2-Fluoro-4-(trans-4′-pentylcyclohexyl)benzoic acid2,3-difluoro-4-(trans-4-propylcyclohexyl)phenylester (No. 1-2-89)

Chemical shift δ (ppm); 8.01(t, 1H), 7.12(dd, 1H), 7.05(dd, 1H),7.01-6.94(m, 2H), 2.84(tt, 1H), 2.55(tt, 1H), 1.93-1.87(m, 8H),1.53-1.41(m, 4H), 1.37-1.20(m, 14H), 1.13-1.02(m, 4H), and 0.92-0.89(m,6H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-2-89) were as follows.

Transition temperature: Cr₁ 76.4 Cr₂ 99.9 N 289.9 Iso.

T_(NI)=227.3° C., Δε=−3.6, Δn=0.149.

4′-Pentylbiphenyl-4-carboxylic acid2,3-difluoro-4-(trans-4-propylcyclohexyl)phenylester (No. 1-2-143)

Chemical shift δ (ppm); 8.25(d, 2H), 7.73(d, 2H), 7.58(d, 2H), 7.30(d,2H), 7.01-6.97(m, 2H), 2.85(tt, 1H), 2.67(t, 2H), 1.91-1.87(m, 4H),1.68-1.65(m, 2H), 1.52-1.45(m, 2H), 1.38-1.31(m, 7H), 1.25-1.20(m, 2H),1.09(qd, 2H), and 0.92-0.89(m, 6H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), dielectric anisotropy (Δε),and optical anisotropy (Δn). The physical property-values of thecompound (No. 1-2-143) were as follows.

Transition temperature: Cr₁ 119.0 N 296.8 Iso.

T_(NI)=243.9° C., Δε=−2.9, Δn=0.220.

trans-4′-Pentylbicyclohexyl-trans-4-carboxylic acid2,3-difluoro-4-(trans-4-propylcyclohexyl)phenylester (No. 1-2-203)

Chemical shift δ (ppm); 7.42(d, 2H), 7.26(d, 2H), 7.16(t, 1H), 6.93(t,1H), 2.63(t, 2H), 2.54(tt, 1H), 2.19(d, 2H), 1.88-1.86(m, 2H),1.78-1.64(m, 6H), 1.61-1.52(m, 2H), 1.32-1.20(m, 6H), 1.18-0.96(m, 12H),and 0.90-0.82(m, 5H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-2-203) were as follows.

Transition temperature: Cr 77.3 SmA 147.0 N 307.3 Iso.

T_(NI)=249.3° C., Δε=−3.2, Δn=0.154.

trans-4′-Propylbicyclohexyl-trans-4-carboxylic acid4′-butoxy-2,3,3′-trifluorobiphenyl-4-ylester (No. 1-2-209)

Chemical shift δ (ppm); 7.26(d, 1H), 7.22(d, 1H), 7.13(t, 1H), 7.02(t,1H), 6.94(t, 1H), 4.08(t, 2H), 2.54(tt, 1H), 2.19(d, 2H), 1.88-1.71(m,8H), 1.61-1.52(m, 4H), 1.33-1.27(m, 2H), 1.16-0.96(m, 12H), and0.89-0.82(m, 5H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-2-209) were as follows.

Transition temperature: Cr 72.0 SmA 212.3 N 303.2 Iso.

T_(NI)=244.6° C., Δε=−4.8, Δn=0.167.

4′-Pentylbiphenyl-4-carboxylic acid2,3-difluoro-4′-propylbiphenyl-4-ylester (No. 1-2-323)

Chemical shift δ (ppm); 8.28(d, 2H), 7.75(d, 2H), 7.59(d, 2H), 7.47(d,2H), 7.32-7.28(m, 4H), 7.28(t, 1H), 7.12(t, 1H), 2.69-2.63(m, 4H),1.73-1.64(m, 4H), 1.39-1.35(m, 4H), 0.99(t, 3H), and 0.92(t, 3H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-2-323) were as follows.

Transition temperature: Cr 132.4 N 291.4 Iso.

T_(NI)=238.6° C., Δε=−1.9, Δn=0.277.

4-Pentyl benzoic acid2,3-difluoro-4-(trans-4′-propylbicyclohexyl-trans-4-yl)phenylesterbiphenyl-4-ylester (No. 2-2-203)

Chemical shift δ (ppm); 8.11(d, 2H), 7.32(d, 2H), 7.10-6.93(m, 2H),2.82(tt, 1H), 2.70(t, 2H), 1.92-1.84(m, 4H), 1.78-1.73(m, 4H),1.67-1.64(m, 2H), 1.47-1.42(m, 2H), 1.39-1.28(m, 6H), 1.23-0.97(m, 9H),and 0.92-0.85(m, 8H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), dielectric anisotropy (Δε),and optical anisotropy (Δn). The physical property-values of thecompound (No. 2-2-203) were as follows.

Transition temperature: Cr 117.7 N 302.0 Iso.

T_(NI)=240.6° C., Δε=−2.6, Δn=0.154.

Example 13

The compounds (No. 1-2-1) to (No. 1-2-410), and the compounds (No.2-2-1) to (No. 2-2-410), which are shown in Table 57 to Table 112, canbe synthesized by synthesis methods similar to those described inExamples 9, 10, 11, and 12.

TABLE 57 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-1 CH₃

— — —

CH₃ 1-2-2 CH₃

— — —

C₂H₅ 1-2-3 CH₃

— — —

C₃H₇ 1-2-4 CH₃

— — —

C₄H₉ 1-2-5 CH₃

— — —

C₅H₁₁ 1-2-6 C₂H₅

— — —

CH₃ 1-2-7 C₂H₅

— — —

C₂H₅ 1-2-8 C₂H₅

— — —

C₃H₇ 1-2-9 C₂H₅

— — —

C₄H₉ 1-2-10 C₂H₅

— — —

C₅H₁₁ 1-2-11 C₃H₇

— — —

CH₃ 1-2-12 C₃H₇

— — —

C₂H₅ 1-2-13 C₃H₇

— — —

C₃H₇ 1-2-14 C₃H₇

— — —

C₄H₉ 1-2-15 C₃H₇

— — —

C₅H₁₁

TABLE 58 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-16 C₄H₉

— — —

CH₃ 1-2-17 C₄H₉

— — —

C₂H₅ 1-2-18 C₄H₉

— — —

C₃H₇ 1-2-19 C₄H₉

— — —

C₄H₉ 1-2-20 C₄H₉

— — —

C₅H₁₁ 1-2-21 C₅H₁₁

— — —

CH₃ 1-2-22 C₅H₁₁

— — —

C₂H₅ 1-2-23 C₅H₁₁

— — —

C₃H₇ Cr 55.2 SmC 74.9 SmA 179.6 N 307.2 Iso T_(NI): 255.9° C., Δ ε:−3.6, Δ n: 0.114 1-2-24 C₅H₁₁

— — —

C₄H₉ 1-2-25 C₅H₁₁

— — —

C₅H₁₁ 1-2-26 C₂H₅O

— — —

C₄H₉ 1-2-27 C₅H₁₁

— — —

OC₂H₅ Cr 57.0 SmB 161.9 SmC 174.4 N 300.8 Iso T_(NI): 239.3° C., Δ ε:−3.9, Δ n: 0.109 1-2-28 C₂H₅O

— — —

OC₄H₉ 1-2-29 CH₂═CH

— — —

C₃H₇ 1-2-30 CH₂═CH

— — —

C₅H₁₁

TABLE 59 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-31 CH₃CH═CH

— — —

C₃H₇ 1-2-32 CH₃CH═CH

— — —

C₅H₁₁ 1-2-33 CH₂═CHC₂H₄

— — —

C₃H₇ 1-2-34 CH₂═CHC₂H₄

— — —

C₅H₁₁ 1-2-35 CH₃CH═CH

— — —

C₂H₅ 1-2-36 CH₃CH═CH

— — —

C₃H₇ 1-2-37 CH₃CH═CHC₂H₄

— — —

CH₃ 1-2-38 CH₃CH═CHC₂H₄

— — —

C₂H₅ 1-2-39 C₃H₇

— — —

CH═CH₂ 1-2-40 C₅H₁₁

— — —

CH═CH₂ 1-2-41 C₃H₇

— — —

CH═CHCH₃ 1-2-42 C₄H₉

— — —

CH═CHCH₃ 1-2-43 C₂H₅

— — —

C₂H₄CH═CH₂ 1-2-44 C₃H₇

— — —

C₂H₄CH═CH₂ 1-2-45 CH₃

— — —

CH═CHC₃H₇

TABLE 60 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-46 C₂H₅

— — —

CH═CHC₃H₇ 1-2-47 C₂H₅

— — —

C₂H₄CH═CHCH₃ 1-2-48 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-2-49 CH₂═CH

— — —

C₂H₄CH═CH₂ 1-2-50 CH₃CH═CH

— — —

CH═CH₂ 1-2-51 C₃H₇OCH₂

— — —

C₃H₇ 1-2-52 C₅H₁₁

— — —

OC₂H₄CH═CH₂ 1-2-53 C₃H₇

CH₂CH₂ — —

C₂H₅ 1-2-54 C₅H₁₁

(CH₂₎₄ — —

C₃H₇ 1-2-55 C₃H₇

CH₂O — —

C₂H₅ 1-2-56 C₅H₁₁

OCH₂ — —

C₃H₇ 1-2-57 C₂H₅

COO — —

C₄H₉ 1-2-58 C₇H₁₅

OCO — —

H 1-2-59 C₂H₅

CF₂O — —

C₆H₁₃ 1-2-60 CH₃

OCF₂ — —

C₂H₅

TABLE 61 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-61 CH₃

— — —

CH₃ 1-2-62 CH₃

— — —

C₂H₅ 1-2-63 CH₃

— — —

C₃H₇ 1-2-64 CH₃

— — —

C₄H₉ 1-2-65 CH₃

— — —

C₅H₁₁ 1-2-66 C₂H₅

— — —

CH₃ 1-2-67 C₂H₅

— — —

C₂H₅ 1-2-68 C₂H₅

— — —

C₃H₇ 1-2-69 C₂H₅

— — —

C₄H₉ 1-2-70 C₂H₅

— — —

C₅H₁₁ 1-2-71 C₃H₇

— — —

CH₃ 1-2-72 C₃H₇

— — —

C₂H₅ 1-2-73 C₃H₇

— — —

C₃H₇ 1-2-74 C₃H₇

— — —

C₄H₉ 1-2-75 C₃H₇

— — —

C₅H₁₁

TABLE 62 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-76 C₄H₉

— — —

CH₃ 1-2-77 C₄H₉

— — —

C₂H₅ 1-2-78 C₄H₉

— — —

C₃H₇ 1-2-79 C₄H₉

— — —

C₄H₉ 1-2-80 C₄H₉

— — —

C₅H₁₁ 1-2-81 C₅H₁₁

— — —

CH₃ 1-2-82 C₅H₁₁

— — —

C₂H₅ 1-2-83 C₅H₁₁

— — —

C₃H₇ Cr₁ 65.5 Cr₂ 113.0 N 297.9 Iso T_(NI): 243.9° C., Δ ε: −2.8, Δ n:0.154 1-2-84 C₅H₁₁

— — —

C₄H₉ 1-2-85 C₅H₁₁

— — —

C₃H₇ 1-2-86 C₂H₅O

— — —

C₄H₉ 1-2-87 C₅H₁₁

— — —

OC₂H₅ 1-2-88 C₂H₅O

— — —

OC₄H₉ 1-2-89 C₅H₁₁

— — —

C₃H₇ Cr₁ 76.4 Cr₂ 99.9 N 289.9 Iso T_(NI): 227.3° C., Δ ε: −3.6, Δ n:0.149 1-2-90 C₃H₇

— — —

C₅H₁₁

TABLE 63 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-91 C₂H₅

— — —

C₄H₉ 1-2-92 C₅H₁₁

— — —

C₂H₅ 1-2-93 CH₂═CH

— — —

C₃H₇ 1-2-94 CH₂═CH

— — —

C₅H₁₁ 1-2-95 CH₃CH═CH

— — —

C₂H₅ 1-2-96 CH₂═CH₂H₄

— — —

C₃H₇ 1-2-97 C₃H₇CH═CH

— — —

CH₃ 1-2-98 CH₃CH═CHC₂H₄

— — —

C₂H₅ 1-2-99 C₃H₇

— — —

CH═CH₂ 1-2-100 C₅H₁₁

— — —

CH═CH₂ 1-2-101 C₃H₇

— — —

CH═CHCH₃ 1-2-102 C₄H₉

— — —

CH═CHCH₃ 1-2-103 C₂H₅

— — —

C₂H₄CH═CH₂ 1-2-104 C₃H₇

— — —

C₂H₄CH═CH₂ 1-2-105 CH₃

— — —

CH═CHC₃H₇

TABLE 64 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-106 C₂H₅

— — —

CH═CHC₃H₇ 1-2-107 C₂H₅

— — —

C₂H₄CH═CHCH₃ 1-2-108 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-2-109 CH₂═CH

— — —

C₂H₄CH═CH₂ 1-2-110 CH₃CH═CH

— — —

CH═CH₂ 1-2-111 C₅H₁₁OCH₂O

— — —

C₃H₇ 1-2-112 C₃H₇

— — —

OC₂H₄CH═CH₂ 1-2-113 C₄H₉

CH₂CH₂ — —

C₂H₅ 1-2-114 C₅H₁₁

CH₂CH₂ — —

C₃H₇ 1-2-115 C₃H₇

CH₂O — —

C₂H₅ 1-2-116 C₅H₁₁

OCH₂ — —

C₆H₁₃ 1-2-117 C₅H₁₁

COO — —

C₄H₉ 1-2-118 C₂H₅

OCO — —

C₄H₉ 1-2-119 C₂H₅

CF₂O — —

CH₃ 1-2-120 C₄H₉

OCF₂ — —

C₂H₅

TABLE 65 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-121 CH₃

— — —

CH₃ 1-2-122 CH₃

— — —

C₂H₅ 1-2-123 CH₃

— — —

C₃H₇ 1-2-124 CH₃

— — —

C₄H₉ 1-2-125 CH₃

— — —

C₅H₁₁ 1-2-126 C₂H₅

— — —

CH₃ 1-2-127 C₂H₅

— — —

C₂H₅ 1-2-128 C₂H₅

— — —

C₃H₇ 1-2-129 C₂H₅

— — —

C₄H₉ 1-2-130 C₂H₅

— — —

C₅H₁₁ 1-2-131 C₃H₇

— — —

CH₃ 1-2-132 C₃H₇

— — —

C₂H₅ 1-2-133 C₃H₇

— — —

C₃H₇ 1-2-134 C₃H₇

— — —

C₄H₉ 1-2-135 C₃H₇

— — —

C₅H₁₁

TABLE 66 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-136 C₄H₉

— — —

CH₃ 1-2-137 C₄H₉

— — —

C₂H₅ 1-2-138 C₄H₉

— — —

C₃H₇ 1-2-139 C₄H₉

— — —

C₄H₉ 1-2-140 C₄H₉

— — —

C₅H₁₁ 1-2-141 C₅H₁₁

— — —

CH₃ 1-2-142 C₅H₁₁

— — —

C₂H₅ 1-2-143 C₅H₁₁

— — —

C₃H₇ Cr 119.0 N 296.8 Iso T_(NI): 243.9° C., Δ ε:-2.9, Δ n: 0.2201-2-144 C₅H₁₁

— — —

C₄H₉ 1-2-145 C₅H₁₁

— — —

C₃H₇ 1-2-146 C₂H₅O

— — —

C₄H₉ 1-2-147 C₅H₁₁

— — —

OC₂H₅ 1-2-148 C₂H₅O

— — —

OC₄H₉ 1-2-149 C₅H₁₁

— — —

C₃H₇ 1-2-150 C₃H₇

— — —

C₅H₁₁

TABLE 67 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-151 C₂H₅

— — —

C₄H₉ 1-2-152 C₅H₁₁

— — —

C₂H₅ 1-2-153 CH₂═CH

— — —

C₃H₇ 1-2-154 CH₂═CH

— — —

C₅H₁₁ 1-2-155 CH₃CH═CH

— — —

C₂H₅ 1-2-156 CH₂═CHC₂H₄

— — —

C₃H₇ 1-2-157 C₃H₇CH═CH

— — —

C₄H₉ 1-2-158 CH₃CH═CHC₂H₄

— — —

C₂H₅ 1-2-159 C₃H₇

— — —

CH═CH₂ 1-2-160 C₅H₁₁

— — —

CH═CH₂ 1-2-161 C₃H₇

— — —

CH═CHCH₃ 1-2-162 C₄H₉

— — —

CH═CHCH₃ 1-2-163 C₃H₇

— — —

C₂H₄CH═CH₂ 1-2-164 C₃H₇

— — —

C₂H₄CH═CH₂ 1-2-165 C₄H₉

— — —

CH═CHC₃H₇

TABLE 68 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-166 C₂H₅

— — —

CH═CHC₃H₇ 1-2-167 C₂H₅

— — —

C₂H₄CH═CHCH₃ 1-2-168 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-2-169 CH₂═CH

— — —

CH═CH₂ 1-2-170 CH₃CH═CH

— — —

C₂H₄CH═CH₂ 1-2-171 CH₃OCH₂

— — —

C₃H₇ 1-2-172 C₂H₅

— — —

OC₂H₄CH═CH₂ 1-2-173 C₃H₇

CH₂CH₂ — —

C₂H₅ 1-2-174 C₅H₁₁

CH₂CH₂ — —

C₃H₇ 1-2-175 C₃H₇

CH₂O — —

C₃H₇ 1-2-176 C₃H₇

OCH₂ — —

CH₃ 1-2-177 C₅H₁₁

COO — —

C₄H₉ 1-2-178 C₂H₅

OCO — —

C₃H₇ 1-2-179 C₂H₅

CF₂O — —

C₇H₁₅ 1-2-180 C₄H₉

OCF₂ — —

C₂H₅

TABLE 69 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-181 CH₃

— — —

CH₃ 1-2-182 CH₃

— — —

C₂H₅ 1-2-183 CH₃

— — —

C₃H₇ 1-2-184 CH₃

— — —

C₄H₉ 1-2-185 CH₃

— — —

C₅H₁₁ 1-2-186 C₂H₅

— — —

CH₃ 1-2-187 C₂H₅

— — —

C₂H₅ 1-2-188 C₂H₅

— — —

C₃H₇ 1-2-189 C₂H₅

— — —

C₄H₉ 1-2-190 C₂H₅

— — —

C₅H₁₁ 1-2-191 C₃H₇

— — —

CH₃ 1-2-192 C₃H₇

— — —

C₂H₅ 1-2-193 C₃H₇

— — —

C₃H₇ 1-2-194 C₃H₇

— — —

C₄H₉ 1-2-195 C₃H₇

— — —

C₅H₁₁

TABLE 70 ( 1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-196 C₄H₉

— — —

CH₃ 1-2-197 C₄H₉

— — —

C₂H₅ 1-2-198 C₄H₉

— — —

C₃H₇ 1-2-199 C₄H₉

— — —

C₄H₉ 1-2-200 C₄H₉

— — —

C₅H₁₁ 1-2-201 C₅H₁₁

— — —

CH₃ 1-2-202 C₅H₁₁

— — —

C₂H₅ 1-2-203 C₅H₁₁

— — —

C₃H₇ Cr 77.3 SmA 147.0 N 307.3 Iso T_(NI): 249.3° C., Δ ε: -3.2, Δn:0.154 1-2-204 C₅H₁₁

— — —

C₄H₉ 1-2-205 C₅H₁₁

— — —

C₅H₁₁ 1-2-206 C₂H₅O

— — —

C₄H₉ 1-2-207 C₅H₁₁

— — —

OC₂H₅ 1-2-208 C₂H₅O

— — —

OC₄H₉ 1-2-209 C₃H₇

— — —

OC₄H₉ Cr 72.0 SmA 212.3 N 303.2 Iso T_(NI): 244.6° C., Δ ε:-4.8, Δn:0.167 1-2-210 C₅H₁₁

— — —

OC₂H₅

TABLE 71 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-211 C₃H₇

— — —

C₅H₁₁ 1-2-212 C₅H₁₁

— — —

C₂H₅ 1-2-213 C₄H₉O

— — —

C₃H₇ 1-2-214 CH₂═CH

— — —

C₅H₁₁ 1-2-215 CH₂═CH

— — —

C₂H₅ 1-2-216 CH₂═CHC₂H₄

— — —

C₃H₇ 1-2-217 CH₃CH═CH

— — —

CH₃ 1-2-218 CH₂═CHC₂H₄

— — —

C₂H₅ 1-2-219 C₃H₇CH═CH

— — —

C₃H₇ 1-2-220 CH₃CH═CHC₂H₄

— — —

C₄H₉ 1-2-221 CH₃

— — —

CH₂OC₃H₇ 1-2-222 C₄H₉

— — —

CH₂CH₂F 1-2-223 C₂H₅

— — —

CH═CHCH₃ 1-2-224 C₃H₇

— — —

CH═CHC₃H₇ 1-2-225 C₃H₇

— — —

C₂H₄CH═CH₂

TABLE 72 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-226 C₂H₅

— — —

C₂H₄CH═CH₂ 1-2-227 C₅H₁₁

— — —

C₂H₄CH═CHCH₃ 1-2-228 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-2-229 CH₂═CH

— — —

C₂H₄CH═CH₂ 1-2-230 CH₃CH═CH

— — —

C₂H₄CH═CH₂ 1-2-231 C₃H₇OCH₂

— — —

C₃H₇ 1-2-232 C₃H₇

— — —

OC₂H₄CH═CH₂ 1-2-233 C₅H₁₁

CH₂CH₂ — —

C₂H₅ 1-2-234 C₅H₁₁

CH═CH — —

C₃H₇ 1-2-235 C₃H₇

CH₂O — —

H 1-2-236 C₂H₅

OCH₂ — —

C₃H₇ 1-2-237 C₄H₉

COO — —

C₄H₉ 1-2-238 C₃H₇

OCO — —

C₂H₅ 1-2-239 C₇H₁₅

CF₂O — —

C₂H₅ 1-2-240 C₉H₁₉

OCF₂ — —

CH₃

TABLE 73 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-241 CH₃

— — —

CH₃ 1-2-242 CH₃

— — —

C₂H₅ 1-2-243 CH₃

— — —

C₃H₇ 1-2-244 CH₃

— — —

C₄H₉ 1-2-245 CH₃

— — —

C₅H₁₁ 1-2-246 C₂H₅

— — —

CH₃ 1-2-247 C₂H₅

— — —

C₂H₅ 1-2-248 C₂H₅

— — —

C₃H₇ 1-2-249 C₂H₅

— — —

C₄H₉ 1-2-250 C₂H₅

— — —

C₅H₁₁ 1-2-251 C₃H₇

— — —

CH₃ 1-2-252 C₃H₇

— — —

C₂H₅ 1-2-253 C₃H₇

— — —

C₃H₇ 1-2-254 C₃H₇

— — —

C₄H₉ 1-2-255 C₃H₇

— — —

C₅H₁₁

TABLE 74 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-256 C₄H₉

— — —

CH₃ 1-2-257 C₄H₉

— — —

C₂H₅ 1-2-258 C₄H₉

— — —

C₃H₇ 1-2-259 C₄H₉

— — —

C₄H₉ 1-2-260 C₄H₉

— — —

C₅H₁₁ 1-2-261 C₅H₁₁

— — —

CH₃ 1-2-262 C₅H₁₁

— — —

C₂H₅ 1-2-263 C₅H₁₁

— — —

C₃H₇ Cr 122.5 N 289.8 Iso T_(NI): 232.6° C., Δ ε:-2.0, Δ n: 0.2191-2-264 C₅H₁₁

— — —

C₄H₉ 1-2-265 C₅H₁₁

— — —

C₅H₁₁ 1-2-266 C₂H₅O

— — —

C₄H₉ 1-2-267 C₅H₁₁

— — —

OC₂H₅ 1-2-268 C₂H₅O

— — —

OC₄H₉ 1-2-269 C₃H₇

— — —

OC₄H₉ 1-2-270 C₅H₁₁

— — —

OC₂H₅

TABLE 75 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-271 C₃H₇

— — —

C₅H₁₁ 1-2-272 C₃H₇O

— — —

C₅H₁₁ 1-2-273 C₅H₁₁

— — —

OC₂H₅ 1-2-274 CH₂═CH

— — —

C₅H₁₁ 1-2-275 CH₃CH═CH

— — —

C₂H₅ 1-2-276 CH₂═CHC₂H₄

— — —

C₃H₇ 1-2-277 C₃H₇CH═CH

— — —

CH₃ 1-2-278 CH₃CH═CHC₂H₄

— — —

C₂H₅ 1-2-279 C₂H₅

— — —

CH₂CH₂CHF₂ 1-2-280 CH₂FCH₂CH₂

— — —

C₄H₉ 1-2-281 CH₃

— — —

CH═CH₂ 1-2-282 C₄H₉

— — —

CH═CHCH₃ 1-2-283 C₂H₅

— — —

C₂H₄CH═CH₂ 1-2-284 C₃H₇

— — —

C₂H₄CH═CH₂ 1-2-285 C₃H₇

— — —

CH═CHC₃H₇

TABLE 76 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-286 C₂H₅

— — —

CH═CHC₃H₇ 1-2-287 C₅H₁₁

— — —

C₂H₄CH═CHCH₃ 1-2-288 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-2-289 CH₂═CH

— — —

C₂H₄CH═CH₂ 1-2-290 CH₃CH═CH

— — —

CH═CH₂ 1-2-291 C₂H₅OCH₂

— — —

C₃H₇ 1-2-292 C₃H₇

— — —

OC₂H₄CH═CH₂ 1-2-293 C₃H₇

CH₂CH₂ — —

C₂H₅ 1-2-294 C₂H₅

CH₂CH₂ — —

C₃H₇ 1-2-295 C₃H₇

CH₂O — —

C₂H₅ 1-2-296 C₂H₅

OCH₂ — —

C₃H₇ 1-2-297 C₄H₉

COO — —

C₄H₉ 1-2-298 C₃H₇

OCO — —

H 1-2-299 C₂H₅

CF₂O — —

C₇H₁₅ 1-2-300 CH₃

OCF₂ — —

C₂H₅

TABLE 77 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-301 CH₃

— — —

CH₃ 1-2-302 CH₃

— — —

C₂H₅ 1-2-303 CH₃

— — —

C₃H₇ 1-2-304 CH₃

— — —

C₄H₉ 1-2-305 CH₃

— — —

C₅H₁₁ 1-2-306 C₂H₅

— — —

CH₃ 1-2-307 C₂H₅

— — —

C₂H₅ 1-2-308 C₂H₅

— — —

C₃H₇ 1-2-309 C₂H₅

— — —

C₄H₉ 1-2-310 C₂H₅

— — —

C₅H₁₁ 1-2-311 C₃H₇

— — —

CH₃ 1-2-312 C₃H₇

— — —

C₂H₅ 1-2-313 C₃H₇

— — —

C₃H₇ 1-2-314 C₃H₇

— — —

C₄H₉ 1-2-315 C₃H₇

— — —

C₅H₁₁

TABLE 78 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-316 C₄H₉

— — —

CH₃ 1-2-317 C₄H₉

— — —

C₂H₅ 1-2-318 C₄H₉

— — —

C₃H₇ 1-2-319 C₄H₉

— — —

C₄H₉ 1-2-320 C₄H₉

— — —

C₅H₁₁ 1-2-321 C₅H₁₁

— — —

CH₃ 1-2-322 C₅H₁₁

— — —

C₂H₅ 1-2-323 C₅H₁₁

— — —

C₃H₇ Cr 132.4 N 291.4 Iso T_(NI): 238.6° C., Δ ε:-1.9, Δ n:0.277 1-2-324C₅H₁₁

— — —

C₄H₉ 1-2-325 C₅H₁₁

— — —

C₅H₁₁ 1-2-326 C₂H₅O

— — —

C₄H₉ 1-2-327 C₅H₁₁

— — —

OC₂H₅ 1-2-328 C₂H₅O

— — —

OC₄H₉ 1-2-329 C₃H₇

— — —

OC₄H₉ 1-2-330 C₅H₁₁

— — —

OC₂H₅

Table 79 (1-2)

No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb Physical property values 1-2-331 C₃H₇

— — —

C₅H₁₁ 1-2.332 C₃H₇O

— — —

OC₂H₅ 1-2-333 C₅H₁₁

— — —

OC₂H₅ 1-2-334 C₂H₅O

— — —

C₅H₁₁ 1-2-335 C₄H₉

— — —

C₂H₅ 1-2-336 C₂H₅O

— — —

OC₄H₉ 1-2-337 CH₂═CH

— — —

CH₃ 1-2-338 CH₃CH═CH

— — —

C₂H₅ 1-2-339 CH₂═CHC₂H₄

— — —

C₃H₇ 1-2-340 C₃H₇CH═CH

— — —

C₄H₉ 1-2-341 CH₃CH═CHC₂H₄

— — —

CH₃ 1-2-342 C₄H₉

— — —

CH═CH₂ 1-2-343 C₂H₅

— — —

CH═CHCH₃ 1-2-344 C₃H₇

— — —

CH═CHC₃H₇ 1-2-345 C₃H₇

— — —

C₂H₄CH═CH₂

TABLE 80 (1-2)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-2-346 C₂H₅

— — —

C₂H₄CH═CH₂ 1-2-347 C₅H₁₁

— — —

C₂H₄CH═CHCH₃ 1-2-348 C₃H₇

— — —

C₂H₄CH═CHCH₃ 1-2-349 CH₃CH═CHC₂H₄

— — —

C₂H₄CH═CH₂ 1-2-350 CH₂═CHC₂H₄O

— — —

C₄H₉CH═CHCH₃ 1-2-351 C₄H₉OCH₂

— — —

C₃H₇ 1-2-352 C₃H₇

— — —

OC₂H₄CH═CH₂ 1-2-353 C₃H₇

CH₂CH₂ — —

C₂H₅ 1-2-354 C₂H₅

C≡C — —

C₃H₇ 1-2-355 C₃H₇

CH₂O — —

C₂H₅ 1-2-356 C₂H₅

OCH₂ — —

C₃H₇ 1-2-357 C₄H₉O

COO — —

C₄H₉ 1-2-358 C₃H₇

OCO — —

C₇H₁₅ 1-2-359 C₂H₅

CF₂O — —

C₄H₉ 1-2-360 CH₃

OCF₂ — —

C₂H₅

TABLE 81 (1-2)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-2-361 C₃H₇

— — —

C₂H₅ 1-2-362 C₅H₁₁

— — —

C₄H₉ 1-2-363 CH₃

— — —

C₃H₇ 1-2-364 C₄H₉

— — —

C₂H₅ 1-2-365 CH₃

— — —

OC₂H₅ 1-2-366 C₂H₅

— — —

C₂H₅ 1-2-367 C₂H₅

— — —

C₃H₇ 1-2-368 C₂H₅

— — —

C₃H₇ 1-2-369 C₂H₅O

— — —

C₄H₉ 1-2-370 C₂H₅

— — —

C₅H₁₁ 1-2-371 C₃H₇

— — —

C₄H₉ 1-2-372 C₃H₇

— — —

C₂H₅ 1-2-373 C₂H₅

— — —

C₅H₁₁ 1-2-374 C₃H₇

— — —

C₄H₉ 1-2-375 C₃H₇

— — —

C₅H₁₁

TABLE 82 (1-2)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-2-376 C₄H₉

— — —

C₅H₁₁ 1-2-377 C₅H₁₁

— — —

C₂H₅ 1-2-378 C₄H₉

— — —

C₃H₇ 1-2-379 C₃H₇

— — —

C₄H₉ 1-2-380 C₅H₁₁

— — —

C₃H₇ 1-2-381 C₃H₇

— — —

OC₄H₉ 1-2-382 C₃H₇

— — —

C₂H₅ 1-2-383 C₅H₁₁

— — —

C₃H₇ 1-2-384 C₅H₁₁

— — —

C₄H₉ 1-2-385 C₂H₅O

— — —

C₅H₁₁ 1-2-386 C₂H₅O

— — —

C₄H₉ 1-2-387 C₅H₁₁

— — —

OC₂H₅ 1-2-388 C₂H₅O

— — —

C₅H₁₁ 1-2-389 C₅H₁₁

— — —

C₃H₇ 1-2-390 C₃H₇

— — —

C₅H₁₁

TABLE 83 (1-2)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-2-391 C₃H₇

—

—

C₅H₁₁ 1-2-392 C₅H₁₁

—

—

C₃H₇ 1-2-393 C₃H₇

—

—

C₅H₁₁ 1-2-394 C₅H₁₁

—

—

C₃H₇ 1-2-395 C₃H₇

—

—

C₅H₁₁ 1-2-396 C₅H₁₁

—

—

C₃H₇ 1-2-397 C₃H₇

—

—

C₅H₁₁ 1-2-398 C₅H₁₁

—

—

C₃H₇ 1-2-399 C₃H₇

—

—

C₅H₁₁ 1-2-400 C₅H₁₁

CH₂CH₂

—

C₃H₇ 1-2-401 C₃H₇

CH₂CH₂

—

C₅H₁₁ 1-2-402 C₅H₁₁

—

CH₂CH₂

C₃H₇ 1-2-403 C₃H₇

—

CH₂CH₂

C₅H₁₁ 1-2-404 C₅H₁₁

—

—

C₃H₇ 1-2-405 C₃H₇

—

—

C₅H₁₁

TABLE 84 (1-2)

Physical No. Ra A¹ Z¹ A¹ Z¹ A² A³ Rb property values 1-2-406 C₅H₁₁

—

—

C₃H₇ 1-2-407 C₃H₇

—

—

C₅H₁₁ 1-2-408 C₃H₇

—

—

C₅H₁₁ 1-2-409 C₃H₇

—

—

C₅H₁₁ 1-2-410 C₃H₇

—

—

C₅H₁₁

TABLE 85 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-1 CH₃ — —

—

CH₃ 2-2-2 CH₃ — —

—

C₂H₅ 2-2-3 CH₃ — —

—

C₃H₇ 2-2-4 CH₃ — —

—

C₄H₉ 2-2-5 CH₃ — —

—

C₅H₁₁ 2-2-6 C₂H₅ — —

—

CH₃ 2-2-7 C₂H₅ — —

—

C₂H₅ 2-2-8 C₂H₅ — —

—

C₃H₇ 2-2-9 C₂H₅ — —

—

C₄H₉ 2-2-10 C₂H₅ — —

—

C₅H₁₁ 2-2-11 C₃H₇ — —

—

CH₃ 2-2-12 C₃H₇ — —

—

C₂H₅ 2-2-13 C₃H₇ — —

—

C₃H₇ 2-2-14 C₃H₇ — —

—

C₄H₉ 2-2-15 C₃H₇ — —

—

C₅H₁₁

TABLE 86 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-16 C₄H₉ — —

—

CH₃ 2-2-17 C₄H₉ — —

—

C₂H₅ 2-2-18 C₄H₉ — —

—

C₃H₇ 2-2-19 C₄H₉ — —

—

C₄H₉ 2-2-20 C₄H₉ — —

—

C₅H₁₁ 2-2-21 C₅H₁₁ — —

—

CH₃ 2-2-22 C₅H₁₁ — —

—

C₂H₅ 2-2-23 C₅H₁₁ — —

—

C₃H₇ Cr 84.5 SmA 187.8 N 310.3 Iso T_(NI): 251.9° C., Δ ε : −3.2, Δ n:0.114 2-2-24 C₅H₁₁ — —

—

C₄H₉ 2-2-25 C₅H₁₁ — —

—

C₅H₁₁ 2-2-26 C₂H₅O — —

—

C₄H₉ 2-2-27 C₅H₁₁ — —

—

OC₂H₅ 2-2-28 C₂H₅O — —

—

OC₄H₉ 2-2-29 CH₂═CH — —

—

C₃H₇ 2-2-30 CH₂═CH — —

—

C₅H₁₁

TABLE 87 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-31 CH₃CH═CH — —

—

C₃H₇ 2-2-32 CH₃CH═CH — —

—

C₅H₁₁ 2-2-33 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-2-34 CH₂═CHC₂H₄ — —

—

C₅H₁₁ 2-2-35 C₃H₇CH═CH — —

—

C₂H₅ 2-2-36 C₃H₇CH═CH — —

—

C₃H₇ 2-2-37 CH₃CH═CHC₂H₄ — —

—

CH₃ 2-2-38 CH₃CH═CHC₂H₄ — —

—

C₂H₅ 2-2-39 C₃H₇ — —

—

CH═CH₂ 2-2-40 C₅H₁₁ — —

—

CH═CH₂ 2-2-41 C₃H₇ — —

—

CH═CHCH₃ 2-2-42 C₄H₉ — —

—

CH═CHCH₃ 2-2-43 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-2-44 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-2-45 CH₃ — —

—

CH═CHC₃H₇

TABLE 88 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-46 C₂H₅ — —

—

CH═CHC₃H₇ 2-2-47 C₂H₅ — —

—

C₂H₄CH═CHCH₃ 2-2-48 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-2-49 CH₂═CH — —

—

C₂H₄CH═CH₂ 2-2-50 CH₃CH═CH — —

—

CH═CH₂ 2-2-51 C₃H₇OCH₂ — —

—

C₃H₇ 2-2-52 C₅H₁₁ — —

—

OC₂H₄CH═CH₂ 2-2-53 C₃H₇ — —

CH₂CH₂

C₂H₅ 2-2-54 C₅H₁₁ — —

CH═CH

C₃H₇ 2-2-55 C₃H₇ — —

CH₂O

C₂H₅ 2-2-56 C₅H₁₁ — —

OCH₂

C₃H₇ 2-2-57 H — —

COO

C₄H₉ 2-2-58 C₇H₁₅ — —

OCO

C₄H₉ 2-2-59 C₂H₅ — —

CF₂O

C₆H₁₃ 2-2-60 CH₃ — —

OCF₂

C₂H₅

TABLE 89 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-61 CH₃ — —

—

CH₃ 2-2-62 CH₃ — —

—

C₂H₅ 2-2-63 CH₃ — —

—

C₃H₇ 2-2-64 CH₃ — —

—

C₄H₉ 2-2-65 CH₃ — —

—

C₅H₁₁ 2-2-66 C₂H₅ — —

—

CH₃ 2-2-67 C₂H₅ — —

—

C₂H₅ 2-2-68 C₂H₅ — —

—

C₃H₇ 2-2-69 C₂H₅ — —

—

C₄H₉ 2-2-70 C₂H₅ — —

—

C₅H₁₁ 2-2-71 C₃H₇ — —

—

CH₃ 2-2-72 C₃H₇ — —

—

C₂H₅ 2-2-73 C₃H₇ — —

—

C₃H₇ 2-2-74 C₃H₇ — —

—

C₄H₉ 2-2-75 C₃H₇ — —

—

C₅H₁₁

TABLE 90 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-76 C₄H₉ — —

—

CH₃ 2-2-77 C₄H₉ — —

—

C₂H₅ 2-2-78 C₄H₉ — —

—

C₃H₇ 2-2-79 C₄H₉ — —

—

C₄H₉ 2-2-80 C₄H₉ — —

—

C₅H₁₁ 2-2-81 C₅H₁₁ — —

—

CH₃ 2-2-82 C₅H₁₁ — —

—

C₂H₅ 2-2-83 C₅H₁₁ — —

—

C₃H₇ 2-2-84 C₅H₁₁ — —

—

C₄H₉ 2-2-85 C₅H₁₁ — —

—

C₃H₇ 2-2-86 C₂H₅O — —

—

C₄H₉ 2-2-87 C₅H₁₁ — —

—

OC₂H₅ 2-2-88 C₂H₅O — —

—

OC₄H₉ 2-2-89 C₅H₁₁ — —

—

C₃H₇ 2-2-90 C₃H₇ — —

—

C₅H₁₁

TABLE 91 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-91 C₂H₅ — —

—

C₄H₉ 2-2-92 C₅H₁₁ — —

—

C₂H₅ 2-2-93 CH₂═CH — —

—

C₃H₇ 2-2-94 CH₂═CH — —

—

C₅H₁₁ 2-2-95 CH₃CH═CH — —

—

C₂H₅ 2-2-96 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-2-97 C₃H₇CH═CH — —

—

CH₃ 2-2-98 CH₃CH═CHC₂H₄ — —

—

C₂H₅ 2-2-99 C₃H₇ — —

—

CH═CH₂ 2-2-100 C₅H₁₁ — —

—

CH═CH₂ 2-2-101 C₃H₇ — —

—

CH═CHCH₃ 2-2-102 C₄H₉ — —

—

CH═CHCH₃ 2-2-103 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-2-104 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-2-105 CH₃ — —

—

CH═CHC₃H₇

TABLE 92 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-106 C₂H₅ — —

—

CH═CHC₃H₇ 2-2-107 C₂H₅ — —

—

C₂H₄CH═CHCH₃ 2-2-108 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-2-109 CH₂═CH — —

—

C₂H₄CH═CH₂ 2-2-110 CH₃CH═CH — —

—

CH═CH₂ 2-2-111 C₅H₁₁OCH₂ — —

—

C₃H₇ 2-2-112 C₃H₇ — —

—

OC₂H₄CH═CH₂ 2-2-113 C₄H₉ — —

CH₂CH₂

C₂H₅ 2-2-114 C₅H₁₁ — —

CH₂CH₂

C₃H₇ 2-2-115 C₃H₇ — —

CH₂O

C₂H₅ 2-2-116 C₅H₁₁ — —

OCH₂

C₆H₁₃ 2-2-117 C₅H₁₁ — —

COO

C₄H₉ 2-2-118 C₂H₅ — —

OCO

C₄H₉ 2-2-119 C₂H₅ — —

CF₂O

CH₃ 2-2-120 C₄H₉ — —

OCF₂

C₂H₅

TABLE 93 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-121 CH₃ — —

—

CH₃ 2-2-122 CH₃ — —

—

C₂H₅ 2-2-123 CH₃ — —

—

C₃H₇ 2-2-124 CH₃ — —

—

C₄H₉ 2-2-125 CH₃ — —

—

C₅H₁₁ 2-2-126 C₂H₅ — —

—

CH₃ 2-2-127 C₂H₅ — —

—

C₂H₅ 2-2-128 C₂H₅ — —

—

C₃H₇ 2-2-129 C₂H₅ — —

—

C₄H₉ 2-2-130 C₂H₅ — —

—

C₅H₁₁ 2-2-131 C₃H₇ — —

—

CH₃ 2-2-132 C₃H₇ — —

—

C₂H₅ 2-2-133 C₃H₇ — —

—

C₃H₇ 2-2-134 C₃H₇ — —

—

C₄H₉ 2-2-135 C₃H₇ — —

—

C₅H₁₁

TABLE 94 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-136 C₄H₉ — —

—

CH₃ 2-2-137 C₄H₉ — —

—

C₂H₅ 2-2-138 C₄H₉ — —

—

C₃H₇ 2-2-139 C₄H₉ — —

—

C₄H₉ 2-2-140 C₄H₉ — —

—

C₅H₁₁ 2-2-141 C₅H₁₁ — —

—

CH₃ 2-2-142 C₅H₁₁ — —

—

C₂H₅ 2-2-143 C₅H₁₁ — —

—

C₃H₇ 2-2-144 C₅H₁₁ — —

—

C₄H₉ 2-2-145 C₅H₁₁ — —

—

C₅H₁₁ 2-2-146 C₂H₅O — —

—

C₄H₉ 2-2-147 C₅H₁₁ — —

—

OC₂H₅ 2-2-148 C₂H₅O — —

—

OC₄H₉ 2-2-149 C₃H₇ — —

—

OC₄H₉ 2-2-150 C₅H₁₁ — —

—

OC₂H₅

TABLE 95 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-151 C₃H₇ — —

—

C₅H₁₁ 2-2-152 C₃H₇O — —

—

C₅H₁₁ 2-2-153 C₅H₁₁ — —

—

OC₂H₅ 2-2-154 CH₂═CH — —

—

C₅H₁₁ 2-2-155 CH₃CH═CH — —

—

C₂H₅ 2-2-156 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-2-157 C₃H₇CH═CH — —

—

CH₃ 2-2-158 CH₃CH═CHC₂H₄ — —

—

C₂H₅ 2-2-159 C₂H₅ — —

—

CH₂CH₂CHF₂ 2-2-160 CH₂FCH₂CH₂ — —

—

C₄H₉ 2-2-161 CH₃ — —

—

CH═CH₂ 2-2-162 C₄H₉ — —

—

CH═CHCH₃ 2-2-163 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-2-164 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-2-165 C₃H₇ — —

—

CH═CHC₃H₇

TABLE 96 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-166 C₂H₅ — —

—

CH═CHC₃H₇ 2-2-167 C₅H₁₁ — —

—

C₂H₄CH═CHCH₃ 2-2-168 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-2-169 CH₂═CH — —

—

C₂H₄CH═CH₂ 2-2-170 CH₃CH═CH — —

—

CH═CH₂ 2-2-171 C₂H₅OCH₂ — —

—

C₃H₇ 2-2-172 C₃H₇ — —

—

OC₂H₄CH═CH₂ 2-2-173 C₃H₇ — —

CH₂CH₂

C₂H₅ 2-2-174 C₂H₅ — —

CH₂CH₂

C₃H₇ 2-2-175 C₃H₇ — —

CH₂O

C₂H₅ 2-2-176 C₂H₅ — —

OCH₂

C₃H₇ 2-2-177 C₄H₉ — —

COO

C₄H₉ 2-2-178 C₃H₇ — —

OCO

H 2-2-179 C₂H₅ — —

CF₂O

C₇H₁₅ 2-2-180 CH₃ — —

OCF₂

C₂H₅

TABLE 97 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-181 CH₃ — —

—

CH₃ 2-2-182 CH₃ — —

—

C₂H₅ 2-2-183 CH₃ — —

—

C₃H₇ 2-2-184 CH₃ — —

—

C₄H₉ 2-2-185 CH₃ — —

—

C₅H₁₁ 2-2-186 C₂H₅ — —

—

CH₃ 2-2-187 C₂H₅ — —

—

C₂H₅ 2-2-188 C₂H₅ — —

—

C₃H₇ 2-2-189 C₂H₅ — —

—

C₄H₉ 2-2-190 C₂H₅ — —

—

C₅H₁₁ 2-2-191 C₃H₇ — —

—

CH₃ 2-2-192 C₃H₇ — —

—

C₂H₅ 2-2-193 C₃H₇ — —

—

C₃H₇ 2-2-194 C₃H₇ — —

—

C₄H₉ 2-2-195 C₃H₇ — —

—

C₅H₁₁

TABLE 98 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-196 C₄H₉ — —

—

CH₃ 2-2-197 C₄H₉ — —

—

C₂H₅ 2-2-198 C₄H₉ — —

—

C₃H₇ 2-2-199 C₄H₉ — —

—

C₄H₉ 2-2-200 C₄H₉ — —

—

C₅H₁₁ 2-2-201 C₅H₁₁ — —

—

CH₃ 2-2-202 C₅H₁₁ — —

—

C₂H₅ 2-2-203 C₅H₁₁ — —

—

C₃H₇ Cr 117.7 N 302.0 Iso T_(NI): 240.6° C., Δ ε: −2.6, Δ n: 0.1542-2-204 C₅H₁₁ — —

—

C₄H₉ 2-2-205 C₅H₁₁ — —

—

C₃H₇ 2-2-206 C₂H₅O — —

—

C₄H₉ 2-2-207 C₅H₁₁ — —

—

OC₂H₅ 2-2-208 C₂H₅O — —

—

OC₄H₉ 2-2-209 C₅H₁₁ — —

—

C₃H₇ 2-2-210 C₃H₇ — —

—

C₅H₁₁

TABLE 99 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-211 C₂H₅ — —

—

CH₂CH₂F 2-2-212 CH₃OC₂H₄ — —

—

C₂H₅ 2-2-213 CH₂═CH — —

—

C₃H₇ 2-2-214 CH₂═CH — —

—

C₅H₁₁ 2-2-215 CH₃CH═CH — —

—

C₂H₅ 2-2-216 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-2-217 C₃H₇CH═CH — —

—

C₄H₉ 2-2-218 CH₃CH═CHC₂H₄ — —

—

C₂H₅ 2-2-219 C₃H₇ — —

—

CH═CH₂ 2-2-220 C₅H₁₁ — —

—

CH═CH₂ 2-2-221 C₃H₇ — —

—

CH═CHCH₃ 2-2-222 C₄H₉ — —

—

CH═CHCH₃ 2-2-223 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-2-224 C₃H₇ — —

—

C₂H₄CH═CH₂ 2-2-225 C₄H₉ — —

—

CH═CHC₃H₇

TABLE 100 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-226 C₂H₅ — —

—

CH═CHC₃H₇ 2-2-227 C₂H₅ — —

—

C₂H₄CH═CHCH₃ 2-2-228 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-2-229 CH₂═CH — —

—

CH═CH₂ 2-2-230 CH₃CH═CH — —

—

C₂H₄CH═CH₂ 2-2-231 CH₃OCH₂ — —

—

C₃H₇ 2-2-232 C₂H₅ — —

—

OC₂H₄CH═CH₂ 2-2-233 C₅H₁₁ — —

CH₂CH₂

C₂H₅ 2-2-234 C₅H₁₁ — —

CH₂CH₂

C₃H₇ 2-2-235 C₂H₅ — —

CH₂O

C₃H₇ 2-2-236 C₃H₇ — —

OCH₂

CH₃ 2-2-237 C₅H₁₁ — —

COO

C₄H₉ 2-2-238 C₂H₅ — —

OCO

C₃H₇ 2-2-239 C₂H₅ — —

CF₂O

C₆H₁₃ 2-2-240 C₄H₉ — —

OCF₂

C₂H₅

TABLE 101 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-241 CH₃ — —

—

CH₃ 2-2-242 CH₃ — —

—

C₂H₅ 2-2-243 CH₃ — —

—

C₃H₇ 2-2-244 CH₃ — —

—

C₄H₉ 2-2-245 CH₃ — —

—

C₅H₁₁ 2-2-246 C₂H₅ — —

—

CH₃ 2-2-247 C₂H₅ — —

—

C₂H₅ 2-2-248 C₂H₅ — —

—

C₃H₇ 2-2-249 C₂H₅ — —

—

C₄H₉ 2-2-250 C₂H₅ — —

—

C₅H₁₁ 2-2-251 C₃H₇ — —

—

CH₃ 2-2-252 C₃H₇ — —

—

C₂H₅ 2-2-253 C₃H₇ — —

—

C₃H₇ 2-2-254 C₃H₇ — —

—

C₄H₉ 2-2-255 C₃H₇ — —

—

C₅H₁₁

TABLE 102 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-256 C₄H₉ — —

—

CH₃ 2-2-257 C₄H₉ — —

—

C₂H₅ 2-2-258 C₄H₉ — —

—

C₃H₇ 2-2-259 C₄H₉ — —

—

C₄H₉ 2-2-260 C₄H₉ — —

—

C₅H₁₁ 2-2-261 C₅H₁₁ — —

—

CH₃ 2-2-262 C₅H₁₁ — —

—

C₂H₅ 2-2-263 C₅H₁₁ — —

—

C₃H₇ 2-2-264 C₅H₁₁ — —

—

C₄H₉ 2-2-265 C₅H₁₁ — —

—

C₅H₁₁ 2-2-266 C₂H₅O — —

—

C₄H₉ 2-2-267 C₅H₁₁ — —

—

OC₂H₅ 2-2-268 C₂H₅O — —

—

OC₄H₉ 2-2-269 C₃H₇ — —

—

OC₄H₉ 2-2-270 C₅H₁₁ — —

—

OC₂H₅

TABLE 103 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-271 C₃H₇ — —

—

C₅H₁₁ 2-2-272 C₅H₁₁ — —

—

C₂H₅ 2-2-273 C₄H₉O — —

—

C₃H₇ 2-2-274 CH₂═CH — —

—

C₅H₁₁ 2-2-275 CH₃CH═CH — —

—

C₂H₅ 2-2-276 C₃H₇CH═CH — —

—

C₃H₇ 2-2-277 CH₂═CHC₂H₄ — —

—

CH₃ 2-2-278 CH₂═CHC₂H₄ — —

—

C₂H₅ 2-2-279 CH₃CH═CHC₂H₄ — —

—

C₃H₇ 2-2-280 CH₃CH═CHC₂H₄ — —

—

C₄H₉ 2-2-281 C₃H₇ — —

—

CH₂OC₃H₇ 2-2-282 C₄H₉ — —

—

CH₂CH₂F 2-2-283 C₂H₅ — —

—

CH═CH₂ 2-2-284 C₃H₇ — —

—

CH═CHCH₃ 2-2-285 C₃H₇ — —

—

CH═CHC₃H₇

TABLE 104 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-286 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-2-287 C₅H₁₁ — —

—

C₂H₄CH═CH₂ 2-2-288 C₄H₉ — —

—

C₂H₄CH═CHCH₃ 2-2-289 CH₂═CHC₂H₄ — —

—

CH═CH₂ 2-2-290 CH₃CH═CHC₂H₄ — —

—

CH═CHCH₃ 2-2-291 CH₃OCH₂CH₂ — —

—

C₃H₇ 2-2-292 C₃H₇ — —

—

OC₂H₄CH═CH₂ 2-2-293 C₅H₁₁ — —

CH₂CH₂

C₂H₅ 2-2-294 C₅H₁₁ — —

CH₂CH₂

C₃H₇ 2-2-295 C₃H₇ — —

CH₂O

C₅H₁₁ 2-2-296 C₂H₅ — —

OCH₂

C₃H₇ 2-2-297 C₄H₉ — —

COO

C₄H₉ 2-2-298 C₃H₇ — —

OCO

C₂H₅ 2-2-299 C₁₀H₂₁ — —

CF₂O

C₂H₅ 2-2-300 CH₃ — —

OCF₂

CH₃

TABLE 105 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-301 CH₃ — —

—

CH₃ 2-2-302 CH₃ — —

—

C₂H₅ 2-2-303 CH₃ — —

—

C₃H₇ 2-2-304 CH₃ — —

—

C₄H₉ 2-2-305 CH₃ — —

—

C₅H₁₁ 2-2-306 C₂H₅ — —

—

CH₃ 2-2-307 C₂H₅ — —

—

C₂H₅ 2-2-308 C₂H₅ — —

—

C₃H₇ 2-2-309 C₂H₅ — —

—

C₄H₉ 2-2-310 C₂H₅ — —

—

C₅H₁₁ 2-2-311 C₃H₇ — —

—

CH₃ 2-2-312 C₃H₇ — —

—

C₂H₅ 2-2-313 C₃H₇ — —

—

C₃H₇ 2-2-314 C₃H₇ — —

—

C₄H₉ 2-2-315 C₃H₇ — —

—

C₅H₁₁

TABLE 106 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-316 C₄H₉ — —

—

CH₃ 2-2-317 C₄H₉ — —

—

C₂H₅ 2-2-318 C₄H₉ — —

—

C₃H₇ 2-2-319 C₄H₉ — —

—

C₄H₉ 2-2-320 C₄H₉ — —

—

C₅H₁₁ 2-2-321 C₅H₁₁ — —

—

CH₃ 2-2-322 C₅H₁₁ — —

—

C₂H₅ 2-2-323 C₅H₁₁ — —

—

C₃H₇ 2-2-324 C₅H₁₁ — —

—

C₄H₉ 2-2-325 C₅H₁₁ — —

—

C₅H₁₁ 2-2-326 C₂H₅O — —

—

C₄H₉ 2-2-327 C₅H₁₁ — —

—

OC₂H₅ 2-2-328 C₂H₅O — —

—

OC₄H₉ 2-2-329 C₃H₇ — —

—

OC₄H₉ 2-2-330 C₅H₁₁ — —

—

OC₂H₅

TABLE 107 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-331 C₃H₇ — —

—

C₅H₁₁ 2-2-332 C₃H₇O — —

—

OC₂H₅ 2-2-333 C₅H₁₁ — —

—

OC₂H₅ 2-2-334 C₂H₅O — —

—

C₅H₁₁ 2-2-335 C₄H₉ — —

—

C₂H₅ 2-2-336 C₂H₅O — —

—

OC₄H₉ 2-2-337 CH₂═CH — —

—

CH₃ 2-2-338 CH₃CH═CH — —

—

C₂H₅ 2-2-339 CH₂═CHC₂H₄ — —

—

C₃H₇ 2-2-340 C₃H₇CH═CH — —

—

C₄H₉ 2-2-341 CH₃CH═CHC₂H₄ — —

—

CH₃ 2-2-342 C₄H₉ — —

—

CH═CH₂ 2-2-343 C₂H₅ — —

—

CH═CHCH₃ 2-2-344 C₃H₇ — —

—

CH═CHC₃H₇ 2-2-345 C₃H₇ — —

—

C₂H₄CH═CH₂

TABLE 108 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-346 C₂H₅ — —

—

C₂H₄CH═CH₂ 2-2-347 C₅H₁₁ — —

—

C₂H₄CH═CHCH₃ 2-2-348 C₃H₇ — —

—

C₂H₄CH═CHCH₃ 2-2-349 CH₃CH═CHC₂H₄ — —

—

C₂H₄CH═CH₂ 2-2-350 CH₂═CHC₂H₄ — —

—

C₂H₄CH═CHCH₃ 2-2-351 C₄H₉OCH₂ — —

—

C₃H₇ 2-2-352 C₃H₇ — —

—

OC₂H₄CH═CH₂ 2-2-353 C₃H₇ — —

CH₂CH₂

C₂H₅ 2-2-354 C₂H₅ — —

(CH₂)₄

C₃H₇ 2-2-355 C₃H₇ — —

CH₂O

C₂H₅ 2-2-356 C₂H₅ — —

OCH₂

C₃H₇ 2-2-357 C₄H₉O — —

COO

C₄H₉ 2-2-358 C₃H₇ — —

OCO

C₇H₁₅ 2-2-359 C₂H₅ — —

CF₂O

C₄H₉ 2-2-360 CH₃ — —

OCF₂

C₂H₅

TABLE 109 (2-2)

No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb Physical property values 2-2-361 C₃H₇ — —

—

C₅H₁₁ 2-2-362 C₅H₁₁ — —

—

C₂H₅ 2-2-363 CH₃ — —

—

C₃H₇ 2-2-364 C₄H₉ — —

—

C₂H₅ 2-2-365 C₅H₁₁ — —

—

OC₄H₉ 2-2-366 CH₃ — —

—

C₂H₅ 2-2-367 C₂H₅ — —

—

C₃H₇ 2-2-368 C₂H₅ — —

—

C₃H₇ 2-2-369 C₃H₇O — —

—

C₄H₉ 2-2-370 C₂H₅ — —

—

C₅H₁₁ 2-2-371 C₃H₇ — —

—

C₄H₉ 2-2-372 C₃H₇ — —

—

C₂H₅ 2-2-373 C₂H₅ — —

—

C₅H₁₁ 2-2-374 C₃H₇ — —

—

C₄H₉ 2-2-375 C₃H₇ — —

—

C₅H₁₁

TABLE 110 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-376 C₄H₉ — —

—

C₅H₁₁ 2-2-377 C₅H₁₁ — —

—

C₂H₅ 2-2-378 C₄H₉ — —

—

C₃H₇ 2-2-379 C₄H₉ — —

—

C₄H₉ 2-2-380 C₅H₁₁ — —

—

OC₂H₅ 2-2-381 C₅H₁₁ — —

—

OC₄H₉ 2-2-382 C₅H₁₁ — —

—

C₂H₅ 2-2-383 C₃H₇ — —

—

C₃H₇ 2-2-384 C₅H₁₁ — —

—

C₄H₉ 2-2-385 CH₃O — —

—

C₅H₁₁ 2-2-386 C₂H₅O — —

C≡C

C₄H₉ 2-2-387 C₅H₁₁ — —

—

CH₃ 2-2-388 C₄H₉O — —

—

C₅H₁₁ 2-2-389 C₅H₁₁ — —

—

C₃H₇ 2-2-390 C₃H₇ — —

—

C₅H₁₁

TABLE 111 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-391 C₃H₇

—

—

C₅H₁₁ 2-2-392 C₅H₁₁

—

—

C₃H₇ 2-2-393 C₃H₇

—

—

C₅H₁₁ 2-2-394 C₅H₁₁

—

—

C₃H₇ 2-2-395 C₃H₇

—

—

C₅H₁₁ 2-2-396 C₅H₁₁

—

—

C₃H₇ 2-2-397 C₃H₇

—

—

C₅H₁₁ 2-2-398 C₃H₇

—

—

C₂H₅ 2-2-399 C₃H₇

—

—

C₅H₁₁ 2-2-400 C₅H₁₁

CH₂CH₂

—

C₃H₇ 2-2-401 C₃H₇

CH₂CH₂

—

C₅H₁₁ 2-2-402 C₅H₁₁

—

CH₂CH₂

C₃H₇ 2-2-403 C₃H₇

—

CH₂CH₂

C₅H₁₁ 2-2-404 C₅H₁₁

—

—

C₃H₇ 2-2-405 C₃H₇

—

—

C₅H₁₁

TABLE 112 (2-2)

Physical No. Ra A¹ Z¹ A² A³ Z² A⁴ Rb property values 2-2-406 C₅H₁₁

—

—

C₃H₇ 2-2-407 C₃H₇

—

—

C₅H₁₁ 2-2-408 C₃H₇

—

—

C₅H₁₁ 2-2-409 C₃H₇

—

—

C₅H₁₁ 2-2-410 C₃H₇

—

—

C₅H₁₁

Example 14 Synthesis of4-[Difluoro-(trans-4′-pentylbicyclohexyl-3-ene-4-yl)methoxy]-2,3-difluoro-4′-propylbiphenyl(No. 1-3-363)

Under a nitrogen atmosphere,4-Bromo-4-bromodifluoromethyl-trans-4′-pentylbicyclohexyl (18) (10.2 g),2,3-difluoro-4′-propylbiphenyl-4-ol (14) (5.4 g), and potassiumhydroxide (KOH) (3.7 g) were put in a mixed solvent of toluene (25 ml)and DMF (25 ml), and stirred at 111° C. for another 3 hours. Aftercompletion of the reaction had been confirmed by means of gaschromatographic analysis, the reaction liquid was cooled to 25° C.Toluene (50 ml) and water (100 ml) were added to the reaction mixture,and mixed. Then, the mixture was allowed to stand until it had separatedinto an organic phase and an aqueous phase, and an extractive operationinto an organic phase was carried out. The organic phase obtained wasfractionated, washed with water, and dried over anhydrous magnesiumsulfate. The solution obtained was concentrated under reduced pressure,and the residue was purified with a fractional operation by means ofcolumn chromatography using heptane as the eluent and silica gel as thestationary phase powder. The residue obtained was further purified byrecrystallization from a mixed solvent of heptane and Solmix A-11(volume ratio; heptane:Solmix A-11=2:1), and dried, giving 6.3 g of4-[difluoro-(trans-4′-pentylbicyclohexyl-3-ene-4-yl)methoxy]-2,3-difluoro-4′-propylbiphenyl (No. 1-3-363). The yield basedon the compound (14) was 67.0%.

The compound (18) can be synthesized according to a procedure similar tothat for 3-chloro-2-fluoro-4′-propylbiphenyl-4-ol described in WO2006/093189 A, using 1-bromo-2,3-difluoro-4-methoxybenzene as a rawmaterial.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified as4-[difluoro-(trans-4′-pentylbicyclohexyl-3-ene-4-yl)methoxy]-2,3-difluoro-4′-propylbiphenyl. The measurement solvent wasCDCl₃.

Chemical shift δ (ppm); 7.44(d, 2H), 7.27(d, 2H), 7.17-7.12(m, 2H),6.42(s, 1H), 2.64(t, 2H), 2.42-2.37(m, 1H), 2.24-2.21(m, 2H),1.93-1.90(m, 2H), 1.80-1.65(m, 6H), 1.42-1.20(m, 8H), 1.18-1.11(m, 4H),1.15-0.95(m, 5H), and 0.91-0.86(m, 5H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-3-363) were as follows.

Transition temperature: C 51.2 N 207.9 Iso.

T_(NI)=188.6° C., Δn=0.154.

Example 15 Synthesis of4-[difluoro-(trans-4′-pentylbicyclohexyl-trans-4-yl)methoxy]-2,3-difluoro-4′-propylbiphenyl(No. 1-3-203)

The compound (No. 1-3-363) (5.7 g) and palladium on carbon (Pd/C) (0.3g) were put in a mixed solvent of toluene (30 ml) and Solmix A-11 (30ml), and stirred for five days at 25° C. under a hydrogen atmosphere.After completion of the reaction had been confirmed by means of gaschromatographic analysis, palladium on carbon (Pd/C) in the reactionmixed-solution was removed by filtration, and the filtrate was purifiedwith a fractional operation by means of column chromatography usingheptane as the eluent and silica gel as the stationary phase powder. Theproduct was further purified by recrystallization from a mixed solventof heptane and Solmix A-11 (volume ratio; heptane:Solmix A-11═2:1), anddried, giving 3.76 g of4-[difluoro-(trans-4′-pentylbicyclohexyl-trans-4-yl)methoxy]-2,3-difluoro-4′-propylbiphenyl(No. 1-3-203). The yield based on the compound (No. 1-3-363) was 65.7%.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified as4-[difluoro-(trans-4′-pentylbicyclohexyl-trans-4-yl)methoxy]-2,3-difluoro-4′-propylbiphenyl.The measurement solvent was CDCl₃.

Chemical shift δ (ppm); 7.43(d, 2H), 7.26(d, 2H), 7.13(q, 2H), 2.63(t,2H), 2.10-2.06(m, 3H), 1.86(d, 2H), 1.78-1.65(m, 6H), 1.45-1.37(m, 2H),1.33-1.21(m, 6H), 1.17-0.95(m, 12H), and 0.90-0.84(m, 5H).

Measured values of the compound itself were used for the transitiontemperature, and extrapolated values converted from the measured valuesof the sample, in which the compound was mixed in the mother liquidcrystals (i), by means of the extrapolation method described above wereused for the maximum temperature (T_(NI)), the dielectric anisotropy(Δε), and the optical anisotropy (Δn). The physical property-values ofthe compound (No. 1-3-203) were as follows.

Transition temperature: Cr 45.3 SmB 65.9 N 265.4 Iso.

T_(NI)=219.9° C., Δε=−1.55, Δn=0.140.

Example 16

The compounds (No. 1-3-1) to (No. 1-3-390), and the compounds (No.2-3-1) to (No. 2-3-390), which are shown in Table 113 to 164, can besynthesized by synthetic methods similar to those described in Examples14 and 15.

(1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-1 CH₃

—

CH₃ 1-3-2 CH₃

—

C₂H₅ 1-3-3 CH₃

—

C₃H₇ 1-3-4 CH₃

—

C₄H₉ 1-3-5 CH₃

—

C₅H₁₁ 1-3-6 C₂H₅

—

CH₃ 1-3-7 C₂H₅

—

C₂H₅ 1-3-8 C₂H₅

—

C₃H₇ 1-3-9 C₂H₅

—

C₄H₉ 1-3-10 C₂H₅

—

C₅H₁₁ 1-3-11 C₃H₇

—

CH₃ 1-3-12 C₃H₇

—

C₂H₅ 1-3-13 C₃H₇

—

C₃H₇ 1-3-14 C₃H₇

—

C₄H₉ 1-3-15 C₃H₇

—

C₅H₁₁

TABLE 114 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-16 C₄H₉

—

CH₃ 1-3-17 C₄H₉

—

C₂H₅ 1-3-18 C₄H₉

—

C₃H₇ 1-3-19 C₄H₉

—

C₄H₉ 1-3-20 C₄H₉

—

C₅H₁₁ 1-3-21 C₅H₁₁

—

CH₃ 1-3-22 C₅H₁₁

—

C₂H₅ 1-3-23 C₅H₁₁

—

C₃H₇ 1-3-24 C₅H₁₁

—

C₄H₉ 1-3-25 C₅H₁₁

—

C₅H₁₁ 1-3-26 C₂H₅O

—

C₄H₉ 1-3-27 C₅H₁₁

—

OC₂H₅ 1-3-28 C₂H₅O

—

OC₄H₉ 1-3-29 CH₂═CH

—

C₃H₇ 1-3-30 CH₂═CH

—

C₅H₁₁

TABLE 115 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-31 CH₃CH═CH

—

C₃H₇ 1-3-32 CH₃CH═CH

—

C₅H₁₁ 1-3-33 CH₂═CHC₂H₄

—

C₃H₇ 1-3-34 CH₂═CHC₂H₄

—

C₅H₁₁ 1-3-35 C₃H₇CH═CH

—

C₂H₅ 1-3-36 C₃H₇CH═CH

—

C₃H₇ 1-3-37 CH₃CH═CHC₂H₄

—

CH₃ 1-3-38 CH₃CH═CHC₂H₄

—

C₂H₅ 1-3-39 C₃H₇

—

CH═CH₂ 1-3-40 C₅H₁₁

—

CH═CH₂ 1-3-41 C₃H₇

—

CH═CHCH₃ 1-3-42 C₄H₉

—

CH═CHCH₃ 1-3-43 C₂H₅

—

C₂H₄CH═CH₂ 1-3-44 C₃H₇

—

C₂H₄CH═CH₂ 1-3-45 CH₃

—

CH═CHC₃H₇

TABLE 116 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-46 C₂H₅

—

CH═CHC₃H₇ 1-3-47 C₂H₅

—

C₂H₄CH═CHCH₃ 1-3-48 C₃H₇

—

C₂H₄CH═CHCH₃ 1-3-49 CH₂═CH

—

C₂H₄CH═CH₂ 1-3-50 CH₃CH═CH

—

CH═CH₂ 1-3-51 C₃H₇OCH₂

—

C₃H₇ 1-3-52 C₅H₁₁

—

OC₂H₄CH═CH₂ 1-3-53 C₃H₇

CH₂CH₂

C₂H₅ 1-3-54 C₅H₁₁

CH═CH

C₃H₇ 1-3-55 C₃H₇

CH₂O

C₂H₅ 1-3-56 C₅H₁₁

OCH₂

C₃H₇ 1-3-57 C₂H₅

COO

C₄H₉ 1-3-58 C₇H₁₅

OCO

H 1-3-59 C₂H₅

CF₂O

C₆H₁₃ 1-3-60 CH₃

OCF₂

C₂H₅

TABLE 117 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-61 CH₃

—

CH₃ 1-3-62 CH₃

—

C₂H₅ 1-3-63 CH₃

—

C₃H₇ 1-3-64 CH₃

—

C₄H₉ 1-3-65 CH₃

—

C₅H₁₁ 1-3-66 C₂H₅

—

CH₃ 1-3-67 C₂H₅

—

C₂H₅ 1-3-68 C₂H₅

—

C₃H₇ 1-3-69 C₂H₅

—

C₄H₉ 1-3-70 C₂H₅

—

C₅H₁₁ 1-3-71 C₃H₇

—

CH₃ 1-3-72 C₃H₇

—

C₂H₅ 1-3-73 C₃H₇

—

C₃H₇ 1-3-74 C₃H₇

—

C₄H₉ 1-3-75 C₃H₇

—

C₅H₁₁

TABLE 118 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-76 C₄H₉

—

CH₃ 1-3-77 C₄H₉

—

C₂H₅ 1-3-78 C₄H₉

—

C₃H₇ 1-3-79 C₄H₉

—

C₄H₉ 1-3-80 C₄H₉

—

C₅H₁₁ 1-3-81 C₅H₁₁

—

CH₃ 1-3-82 C₅H₁₁

—

C₂H₅ 1-3-83 C₅H₁₁

—

C₃H₇ 1-3-84 C₅H₁₁

—

C₄H₉ 1-3-85 C₅H₁₁

—

C₃H₇ 1-3-86 C₂H₅O

—

C₄H₉ 1-3-87 C₅H₁₁

—

OC₂H₅ 1-3-88 C₂H₅O

—

OC₄H₉ 1-3-89 C₅H₁₁

—

C₃H₇ 1-3-90 C₃H₇

—

C₅H₁₁

TABLE 119 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-91 C₂H₅

—

C₄H₉ 1-3-92 C₅H₁₁

—

C₂H₅ 1-3-93 CH₂═CH

—

C₃H₇ 1-3-94 CH₂═CH

—

C₅H₁₁ 1-3-95 CH₃CH═CH

—

C₂H₅ 1-3-96 CH₂═CHC₂H₄

—

C₃H₇ 1-3-97 C₃H₇CH═CH

—

CH₃ 1-3-98 CH₃CH═CHC₂H₄

—

C₂H₅ 1-3-99 C₃H₇

—

CH═CH₂ 1-3-100 C₅H₁₁

—

CH═CH₂ 1-3-101 C₃H₇

—

CH═CHCH₃ 1-3-102 C₄H₉

—

CH═CHCH₃ 1-3-103 C₂H₅

—

C₂H₄CH═CH₂ 1-3-104 C₃H₇

—

C₂H₄CH═CH₂ 1-3-105 CH₃

—

CH═CHC₃H₇

TABLE 120 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-106 C₂H₅

—

CH═CHC₃H₇ 1-3-107 C₂H₅

—

C₂H₄CH═CHCH₃ 1-3-108 C₃H₇

—

C₂H₄CH═CHCH₃ 1-3-109 CH₂═CH

—

C₂H₄CH═CH₂ 1-3-110 CH₃CH═CH

—

CH═CH₂ 1-3-111 C₅H₁₁OCH₂

—

C₃H₇ 1-3-112 C₃H₇

—

OC₂H₄CH═CH₂ 1-3-113 C₄H₉

CH₂CH₂

C₂H₅ 1-3-114 C₅H₁₁

CH₂CH₂

C₃H₇ 1-3-115 C₃H₇

CH₂O

C₂H₅ 1-3-116 C₅H₁₁

OCH₂

C₆H₁₃ 1-3-117 C₅H₁₁

COO

C₄H₉ 1-3-118 C₂H₅

OCO

C₄H₉ 1-3-119 C₂H₅

CF₂O

CH₃ 1-3-120 C₄H₉

OCF₂

C₂H₅

TABLE 121 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-121 CH₃

—

CH₃ 1-3-122 CH₃

—

C₂H₅ 1-3-123 CH₃

—

C₃H₇ 1-3-124 CH₃

—

C₄H₉ 1-3-125 CH₃

—

C₅H₁₁ 1-3-126 C₂H₅

—

CH₃ 1-3-127 C₂H₅

—

C₂H₅ 1-3-128 C₂H₅

—

C₃H₇ 1-3-129 C₂H₅

—

C₄H₉ 1-3-130 C₂H₅

—

C₅H₁₁ 1-3-131 C₃H₇

—

CH₃ 1-3-132 C₃H₇

—

C₂H₅ 1-3-133 C₃H₇

—

C₃H₇ 1-3-134 C₃H₇

—

C₄H₉ 1-3-135 C₃H₇

—

C₅H₁₁

TABLE 122 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-136 C₄H₉

—

CH₃ 1-3-137 C₄H₉

—

C₂H₅ 1-3-138 C₄H₉

—

C₃H₇ 1-3-139 C₄H₉

—

C₄H₉ 1-3-140 C₄H₉

—

C₅H₁₁ 1-3-141 C₅H₁₁

—

CH₃ 1-3-142 C₅H₁₁

—

C₂H₅ 1-3-143 C₅H₁₁

—

C₃H₇ 1-3-144 C₅H₁₁

—

C₄H₉ 1-3-145 C₅H₁₁

—

C₃H₇ 1-3-146 C₂H₅O

—

C₄H₉ 1-3-147 C₅H₁₁

—

OC₂H₅ 1-3-148 C₂H₅O

—

OC₄H₉ 1-3-149 C₅H₁₁

—

C₃H₇ 1-3-150 C₃H₇

—

C₅H₁₁

TABLE 123 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-151 C₂H₅

—

C₄H₉ 1-3-152 C₅H₁₁

—

C₂H₅ 1-3-153 CH₂═CH

—

C₃H₇ 1-3-154 CH₂═CH

—

C₅H₁₁ 1-3-155 CH₃CH═CH

—

C₂H₅ 1-3-156 CH₂═CHC₂H₄

—

C₃H₇ 1-3-157 C₃H₇CH═CH

—

C₄H₉ 1-3-158 CH₃CH═CHC₂H₄

—

C₂H₅ 1-3-159 C₃H₇

—

CH═CH₂ 1-3-160 C₅H₁₁

—

CH═CH₂ 1-3-161 C₃H₇

—

CH═CHCH₃ 1-3-162 C₄H₉

—

CH═CHCH₃ 1-3-163 C₃H₇

—

C₂H₄CH═CH₂ 1-3-164 C₃H₇

—

C₂H₄CH═CH₂ 1-3-165 C₄H₉

—

CH═CHC₃H₇

TABLE 124 (1-3)

Physical No. Ra A¹ Z¹ A² A³ Rb property values 1-3-166 C₂H₅

—

CH═CHC₃H₇ 1-3-167 C₂H₅

—

C₂H₄CH═CHCH₃ 1-3-168 C₃H₇

—

C₂H₄CH═CHCH₃ 1-3-169 CH₂═CH

—

CH═CH₂ 1-3-170 CH₃CH═CH

—

C₂H₄CH═CH₂ 1-3-171 CH₃OCH₂

—

C₃H₇ 1-3-172 C₂H₅

—

OC₂H₄CH═CH₂ 1-3-173 C₃H₇

CH₂CH₂

C₂H₅ 1-3-174 C₅H₁₁

C≡C

C₃H₇ 1-3-175 C₃H₇

CH₂O

C₃H₇ 1-3-176 C₃H₇

OCH₂

CH₃ 1-3-177 C₅H₁₁

COO

C₄H₉ 1-3-178 C₂H₅

OCO

C₃H₇ 1-3-179 C₂H₅

CF₂O

C₇H₁₅ 1-3-180 C₄H₉

OCF₂

C₂H₅

TABLE 125 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-181 CH₃

—

CH₃ 1-3-182 CH₃

—

C₂H₅ 1-3-183 CH₃

—

C₃H₇ 1-3-184 CH₃

—

C₄H₉ 1-3-185 CH₃

—

C₅H₁₁ 1-3-186 C₂H₅

—

CH₃ 1-3-187 C₂H₅

—

C₂H₅ 1-3-188 C₂H₅

—

C₃H₇ 1-3-189 C₂H₅

—

C₄H₉ 1-3-190 C₂H₅

—

C₅H₁₁ 1-3-191 C₃H₇

—

CH₃ 1-3-192 C₃H₇

—

C₂H₅ 1-3-193 C₃H₇

—

C₃H₇ 1-3-194 C₃H₇

—

C₄H₉ 1-3-195 C₃H₇

—

C₅H₁₁

TABLE 126 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-196 C₄H₉

—

CH₃ 1-3-197 C₄H₉

—

C₂H₅ 1-3-198 C₄H₉

—

C₃H₇ 1-3-199 C₄H₉

—

C₄H₉ 1-3-200 C₄H₉

—

C₅H₁₁ 1-3-201 C₅H₁₁

—

CH₃ 1-3-202 C₅H₁₁

—

C₂H₅ 1-3-203 C₅H₁₁

—

C₃H₇ Cr 45.3 SmB 65.9 N 265.4 Iso T_(NI): 219.9° C., Δ ε: −1.55, Δ n:0.140 1-3-204 C₅H₁₁

—

C₄H₉ 1-3-205 C₅H₁₁

—

C₅H₁₁ 1-3-206 C₂H₅O

—

C₄H₉ 1-3-207 C₅H₁₁

—

OC₂H₅ 1-3-208 C₂H₅O

—

OC₄H₉ 1-3-209 C₃H₇

—

OC₄H₉ 1-3-210 C₅H₁₁

—

OC₂H₅

TABLE 127 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-211 C₃H₇

—

C₅H₁₁ 1-3-212 C₅H₁₁

—

C₂H₅ 1-3-213 C₄H₉O

—

C₃H₇ 1-3-214 CH₂═CH

—

C₅H₁₁ 1-3-215 CH₂═CH

—

C₂H₅ 1-3-216 CH₂═CHC₂H₄

—

C₃H₇ 1-3-217 CH₃CH═CH

—

CH₃ 1-3-218 CH₂═CHC₂H₄

—

C₂H₅ 1-3-219 C₃H₇CH═CH

—

C₃H₇ 1-3-220 CH₃CH═CHC₂H₄

—

C₄H₉ 1-3-221 CH₃

—

CH₂OC₃H₇ 1-3-222 C₄H₉

—

CH₂CH₂F 1-3-223 C₂H₅

—

CH═CHCH₃ 1-3-224 C₃H₇

—

CH═CHC₃H₇ 1-3-225 C₃H₇

—

C₂H₄CH═CH₂

TABLE 128 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-226 C₂H₅

—

C₂H₄CH═CH₂ 1-3-227 C₅H₁₁

—

C₂H₄CH═CHCH₃ 1-3-228 C₃H₇

—

C₂H₄CH═CHCH₃ 1-3-229 CH₂═CH

—

C₂H₄CH═CH₂ 1-3-230 CH₃CH═CH

—

C₂H₄CH═CH₂ 1-3-231 C₃H₇OCH₂

—

C₃H₇ 1-3-232 C₃H₇

—

OC₂H₄CH═CH₂ 1-3-233 C₅H₁₁

CH₂CH₂

C₂H₅ 1-3-234 C₅H₁₁

CH₂CH₂

C₃H₇ 1-3-235 C₃H₇

CH₂O

H 1-3-236 C₂H₅

OCH₂

C₃H₇ 1-3-237 C₄H₉

COO

C₄H₉ 1-3-238 C₃H₇

OCO

C₂H₅ 1-3-239 C₇H₁₅

CF₂O

C₂H₅ 1-3-240 C₉H₁₉

OCF₂

CH₃

TABLE 129 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-241 CH₃

—

CH₃ 1-3-242 CH₃

—

C₂H₅ 1-3-243 CH₃

—

C₃H₇ 1-3-244 CH₃

—

C₄H₉ 1-3-245 CH₃

—

C₅H₁₁ 1-3-246 C₂H₅

—

CH₃ 1-3-247 C₂H₅

—

C₂H₅ 1-3-248 C₂H₅

—

C₃H₇ 1-3-249 C₂H₅

—

C₄H₉ 1-3-250 C₂H₅

—

C₅H₁₁ 1-3-251 C₃H₇

—

CH₃ 1-3-252 C₃H₇

—

C₂H₅ 1-3-253 C₃H₇

—

C₃H₇ 1-3-254 C₃H₇

—

C₄H₉ 1-3-255 C₃H₇

—

C₅H₁₁

TABLE 130 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-256 C₄H₉

—

CH₃ 1-3-257 C₄H₉

—

C₂H₅ 1-3-258 C₄H₉

—

C₃H₇ 1-3-259 C₄H₉

—

C₄H₉ 1-3-260 C₄H₉

—

C₅H₁₁ 1-3-261 C₅H₁₁

—

CH₃ 1-3-262 C₅H₁₁

—

C₂H₅ 1-3-263 C₅H₁₁

—

C₃H₇ 1-3-264 C₅H₁₁

—

C₄H₉ 1-3-265 C₅H₁₁

—

C₅H₁₁ 1-3-266 C₂H₅O

—

C₄H₉ 1-3-267 C₅H₁₁

—

OC₂H₅ 1-3-268 C₂H₅O

—

OC₄H₉ 1-3-269 C₃H₇

—

OC₄H₉ 1-3-270 C₅H₁₁

—

OC₂H₅

TABLE 131 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-271 C₃H₇

—

C₅H₁₁ 1-3-272 C₃H₇O

—

C₅H₁₁ 1-3-273 C₅H₁₁

—

OC₂H₅ 1-3-274 CH₂═CH

—

C₅H₁₁ 1-3-275 CH₃CH═CH

—

C₂H₅ 1-3-276 CH₂═CHC₂H₄

—

C₃H₇ 1-3-277 C₃H₇CH═CH

—

CH₃ 1-3-278 CH₃CH═CHC₂H₄

—

C₂H₅ 1-3-279 C₂H₅

—

CH₂CH₂CHF₂ 1-3-280 CH₂FCH₂CH₂

—

C₄H₉ 1-3-281 CH₃

—

CH═CH₂ 1-3-282 C₄H₉

—

CH═CHCH₃ 1-3-283 C₂H₅

—

C₂H₄CH═CH₂ 1-3-284 C₃H₇

—

C₂H₄CH═CH₂ 1-3-285 C₃H₇

—

CH═CHC₃H₇

TABLE 132 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-286 C₂H₅

—

CH═CHC₃H₇ 1-3-287 C₅H₁₁

—

C₂H₄CH═CHCH₃ 1-3-288 C₃H₇

—

C₂H₄CH═CHCH₃ 1-3-289 CH₂═CH

—

C₂H₄CH═CH₂ 1-3-290 CH₃CH═CH

—

CH═CH₂ 1-3-291 C₂H₅OCH₂

—

C₃H₇ 1-3-292 C₃H₇

—

OC₂H₄CH═CH₂ 1-3-293 C₃H₇

CH₂CH₂

C₂H₅ 1-3-294 C₂H₅

(CH₂)₄

C₃H₇ 1-3-295 C₃H₇

CH₂O

C₂H₅ 1-3-296 C₂H₅

OCH₂

C₃H₇ 1-3-297 C₄H₉

COO

C₄H₉ 1-3-298 C₃H₇

OCO

H 1-3-299 C₂H₅

CF₂O

C₇H₁₅ 1-3-300 CH₃

OCF₂

C₂H₅

TABLE 133 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-301 CH₃

—

CH₃ 1-3-302 CH₃

—

C₂H₅ 1-3-303 CH₃

—

C₃H₇ 1-3-304 CH₃

—

C₄H₉ 1-3-305 CH₃

—

C₅H₁₁ 1-3-306 C₂H₅

—

CH₃ 1-3-307 C₂H₅

—

C₂H₅ 1-3-308 C₂H₅

—

C₃H₇ 1-3-309 C₂H₅

—

C₄H₉ 1-3-310 C₂H₅

—

C₅H₁₁ 1-3-311 C₃H₇

—

CH₃ 1-3-312 C₃H₇

—

C₂H₅ 1-3-313 C₃H₇

—

C₃H₇ 1-3-314 C₃H₇

—

C₄H₉ 1-3-315 C₃H₇

—

C₅H₁₁

TABLE 134 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-316 C₄H₉

—

CH₃ 1-3-317 C₄H₉

—

C₂H₅ 1-3-318 C₄H₉

—

C₃H₇ 1-3-319 C₄H₉

—

C₄H₉ 1-3-320 C₄H₉

—

C₅H₁₁ 1-3-321 C₅H₁₁

—

CH₃ 1-3-322 C₅H₁₁

—

C₂H₅ 1-3-323 C₅H₁₁

—

C₃H₇ 1-3-324 C₅H₁₁

—

C₄H₉ 1-3-325 C₅H₁₁

—

C₅H₁₁ 1-3-326 C₂H₅O

—

C₄H₉ 1-3-327 C₅H₁₁

—

OC₂H₅ 1-3-328 C₂H₅O

—

OC₄H₉ 1-3-329 C₃H₇

—

OC₄H₉ 1-3-330 C₅H₁₁

—

OC₂H₅

TABLE 135 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-331 C₃H₇

—

C₅H₁₁ 1-3-332 C₃H₇O

—

OC₂H₅ 1-3-333 C₅H₁₁

—

OC₂H₅ 1-3-334 C₂H₅O

—

C₅H₁₁ 1-3-335 C₄H₉

—

C₂H₅ 1-3-336 C₂H₅O

—

OC₄H₉ 1-3-337 CH₂═CH

—

CH₃ 1-3-338 CH₃CH═CH

—

C₂H₅ 1-3-339 CH₂═CHC₂H₄

—

C₃H₇ 1-3-340 C₃H₇CH═CH

—

C₄H₉ 1-3-341 CH₃CH═CHC₂H₄

—

CH₃ 1-3-342 C₄H₉

—

CH═CH₂ 1-3-343 C₂H₅

—

CH═CHCH₃ 1-3-344 C₃H₇

—

CH═CHC₃H₇ 1-3-345 C₃H₇

—

C₂H₄CH═CH₂

TABLE 136 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-346 C₂H₅

—

C₂H₄CH═CH₂ 1-3-347 C₅H₁₁

—

C₂H₄CH═CHCH₃ 1-3-348 C₃H₇

—

C₂H₄CH═CHCH₃ 1-3-349 CH₃CH═CHC₂H₄

—

C₂H₄CH═CH₂ 1-3-350 CH₂═CHC₂H₄

—

C₂H₄CH═CHCH₃ 1-3-351 C₄H₉OCH₂

—

C₃H₇ 1-3-352 C₃H₇

—

OC₂H₄CH═CH₂ 1-3-353 C₃H₇

CH₂CH₂

C₂H₅ 1-3-354 C₂H₅

CH₂CH₂

C₃H₇ 1-3-355 C₃H₇

CH₂O

C₂H₅ 1-3-356 C₂H₅

OCH₂

C₃H₇ 1-3-357 C₄H₉O

COO

C₄H₉ 1-3-358 C₃H₇

OCO

C₇H₁₅ 1-3-359 C₂H₅

CF₂O

C₄H₉ 1-3-360 CH₃

OCF₂

C₂H₅

TABLE 137 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-361 C₃H₇

—

C₂H₅ 1-3-362 C₂H₅

—

C₄H₉ 1-3-363 C₅H₁₁

—

C₃H₇ Cr 51.2 N 207.9 Iso T_(NI): 188.6° C., Δ n: 0.154 1-3-364 C₄H₉

—

C₂H₅ 1-3-365 CH₃

—

OC₂H₅ 1-3-366 C₂H₅

—

C₂H₅ 1-3-367 C₂H₅

—

C₃H₇ 1-3-368 C₂H₅

—

C₃H₇ 1-3-369 C₂H₅O

—

C₄H₉ 1-3-370 C₂H₅

—

C₅H₁₁ 1-3-371 C₃H₇

—

C₄H₉ 1-3-372 C₃H₇

—

C₂H₅ 1-3-373 C₂H₅

—

C₅H₁₁ 1-3-374 C₃H₇

—

C₄H₉ 1-3-375 C₃H₇

—

C₅H₁₁

TABLE 138 (1-3)

No. Ra A¹ Z¹ A² A³ Rb Physical property values 1-3-376 C₄H₉

—

C₅H₁₁ 1-3-377 C₅H₁₁

—

C₂H₅ 1-3-378 C₄H₉

—

C₃H₇ 1-3-379 C₄H₉

—

C₄H₉ 1-3-380 C₂H₅O

—

C₅H₁₁ 1-3-381 C₃H₇

—

OC₄H₉ 1-3-382 C₅H₁₁

—

C₂H₅ 1-3-383 C₅H₁₁

—

C₃H₇ 1-3-384 C₅H₁₁

—

C₄H₉ 1-3-385 C₂H₅O

—

C₅H₁₁ 1-3-386 C₄H₉O

—

C₄H₉ 1-3-387 C₅H₁₁

—

OC₂H₅ 1-3-388 C₂H₅O

—

C₅H₁₁ 1-3-389 C₅H₁₁

—

C₃H₇ 1-3-390 C₃H₇

—

C₅H₁₁

TABLE 139 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-1 CH₃

—

CH₃ 2-3-2 CH₃

—

C₂H₅ 2-3-3 CH₃

—

C₃H₇ 2-3-4 CH₃

—

C₄H₉ 2-3-5 CH₃

—

C₅H₁₁ 2-3-6 C₂H₅

—

CH₃ 2-3-7 C₂H₅

—

C₂H₅ 2-3-8 C₂H₅

—

C₃H₇ 2-3-9 C₂H₅

—

C₄H₉ 2-3-10 C₂H₅

—

C₅H₁₁ 2-3-11 C₃H₇

—

CH₃ 2-3-12 C₃H₇

—

C₂H₅ 2-3-13 C₃H₇

—

C₃H₇ 2-3-14 C₃H₇

—

C₄H₉ 2-3-15 C₃H₇

—

C₅H₁₁

TABLE 140 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-16 C₄H₉

—

CH₃ 2-3-17 C₄H₉

—

C₂H₅ 2-3-18 C₄H₉

—

C₃H₇ 2-3-19 C₄H₉

—

C₄H₉ 2-3-20 C₄H₉

—

C₅H₁₁ 2-3-21 C₅H₁₁

—

CH₃ 2-3-22 C₅H₁₁

—

C₂H₅ 2-3-23 C₅H₁₁

—

C₃H₇ 2-3-24 C₅H₁₁

—

C₄H₉ 2-3-25 C₅H₁₁

—

C₅H₁₁ 2-3-26 C₂H₅O

—

C₄H₉ 2-3-27 C₅H₁₁

—

OC₂H₅ 2-3-28 C₂H₅O

—

OC₄H₉ 2-3-29 CH₂═CH

—

C₃H₇ 2-3-30 CH₂═CH

—

C₅H₁₁

TABLE 141 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-31 CH₃CH═CH

—

C₃H₇ 2-3-32 CH₃CH═CH

—

C₅H₁₁ 2-3-33 CH₂═CHC₂H₄

—

C₃H₇ 2-3-34 CH₂═CHC₂H₄

—

C₅H₁₁ 2-3-35 C₃H₇CH═CH

—

C₂H₅ 2-3-36 C₃H₇CH═CH

—

C₃H₇ 2-3-37 CH₃CH═CHC₂H₄

—

CH₃ 2-3-38 CH₃CH═CHC₂H₄

—

C₂H₅ 2-3-39 C₃H₇

—

CH═CH₂ 2-3-40 C₅H₁₁

—

CH═CH₂ 2-3-41 C₃H₇

—

CH═CHCH₃ 2-3-42 C₄H₉

—

CH═CHCH₃ 2-3-43 C₂H₅

—

C₂H₄CH═CH₂ 2-3-44 C₃H₇

—

C₂H₄CH═CH₂ 2-3-45 CH₃

—

CH═CHC₃H₇

TABLE 142 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-46 C₂H₅

—

CH═CHC₃H₇ 2-3-47 C₂H₅

—

C₂H₄CH═CHCH₃ 2-3-48 C₃H₇

—

C₂H₄CH═CHCH₃ 2-3-49 CH₂═CH

—

C₂H₄CH═CH₂ 2-3-50 CH₃CH═CH

—

CH═CH₂ 2-3-51 C₃H₇OCH₂

—

C₃H₇ 2-3-52 C₅H₁₁

—

OC₂H₄CH═CH₂ 2-3-53 C₃H₇

CH₂CH₂

C₂H₅ 2-3-54 C₅H₁₁

CH₂CH₂

C₃H₇ 2-3-55 C₃H₇

CH₂O

C₂H₅ 2-3-56 C₅H₁₁

OCH₂

C₃H₇ 2-3-57 H

COO

C₄H₉ 2-3-58 C₇H₁₅

OCO

C₄H₉ 2-3-59 C₂H₅

CF₂O

C₆H₁₃ 2-3-60 CH₃

OCF₂

C₂H₅

TABLE 143 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-61 CH₃

—

CH₃ 2-3-62 CH₃

—

C₂H₅ 2-3-63 CH₃

—

C₃H₇ 2-3-64 CH₃

—

C₄H₉ 2-3-65 CH₃

—

C₅H₁₁ 2-3-66 C₂H₅

—

CH₃ 2-3-67 C₂H₅

—

C₂H₅ 2-3-68 C₂H₅

—

C₃H₇ 2-3-69 C₂H₅

—

C₄H₉ 2-3-70 C₂H₅

—

C₅H₁₁ 2-3-71 C₃H₇

—

CH₃ 2-3-72 C₃H₁₇

—

C₂H₅ 2-3-73 C₃H₇

—

C₃H₇ 2-3-74 C₃H₇

—

C₄H₉ 2-3-75 C₃H₇

—

C₅H₁₁

TABLE 144 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-76 C₄H₉

—

CH₃ 2-3-77 C₄H₉

—

C₂H₅ 2-3-78 C₄H₉

—

C₃H₇ 2-3-79 C₄H₉

—

C₄H₉ 2-3-80 C₄H₉

—

C₅H₁₁ 2-3-81 C₅H₁₁

—

CH₃ 2-3-82 C₅H₁₁

—

C₂H₅ 2-3-83 C₅H₁₁

—

C₃H₇ 2-3-84 C₅H₁₁

—

C₄H₉ 2-3-85 C₅H₁₁

—

C₃H₇ 2-3-86 C₂H₅O

—

C₄H₉ 2-3-87 C₅H₁₁

—

OC₂H₅ 2-3-88 C₂H₅O

—

OC₄H₉ 2-3-89 C₅H₁₁

—

C₃H₇ 2-3-90 C₃H₇

—

C₅H₁₁

TABLE 145 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-91 C₂H₅

—

C₄H₉ 2-3-92 C₅H₁₁

—

C₂H₅ 2-3-93 CH₂═CH

—

C₃H₇ 2-3-94 CH₂═CH

—

C₅H₁₁ 2-3-95 CH₃CH═CH

—

C₂H₅ 2-3-96 CH₂═CHC₂H₄

—

C₃H₇ 2-3-97 C₃H₇CH═CH

—

CH₃ 2-3-98 CH₃CH═CHC₂H₄

—

C₂H₅ 2-3-99 C₃H₇

—

CH═CH₂ 2-3-100 C₅H₁₁

—

CH═CH₂ 2-3-101 C₃H₇

—

CH═CHCH₃ 2-3-102 C₄H₉

—

CH═CHCH₃ 2-3-103 C₂H₅

—

C₂H₄CH═CH₂ 2-3-104 C₃H₇

—

C₂H₄CH═CH₂ 2-3-105 CH₃

—

CH═CHC₃H₇

TABLE 146 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-106 C₂H₅

—

CH═CHC₃H₇ 2-3-107 C₂H₅

—

C₂H₄CH═CHCH₃ 2-3-108 C₃H₇

—

C₂H₄CH═CHCH₃ 2-3-109 CH₂═CH

—

C₂H₄CH═CH₂ 2-3-110 CH₃CH═CH

—

CH═CH₂ 2-3-111 C₅H₁₁OCH₂

—

C₃H₇ 2-3-112 C₃H₇

—

OC₂H₄CH═CH₂ 2-3-113 C₄H₉

CH₂CH₂

C₂H₅ 2-3-114 C₅H₁₁

CH═CH

C₃H₇ 2-3-115 C₃H₇

CH₂O

C₂H₅ 2-3-116 C₅H₁₁

OCH₂

C₆H₁₃ 2-3-117 C₅H₁₁

COO

C₄H₉ 2-3-118 C₂H₅

OCO

C₄H₉ 2-3-119 C₂H₅

CF₂O

CH₃ 2-3-120 C₄H₉

OCF₂

C₂H₅

TABLE 147 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-121 CH₃

—

CH₃ 2-3-122 CH₃

—

C₂H₅ 2-3-123 CH₃

—

C₃H₇ 2-3-124 CH₃

—

C₄H₉ 2-3-125 CH₃

—

C₅H₁₁ 2-3-126 C₂H₅

—

CH₃ 2-3-127 C₂H₅

—

C₂H₅ 2-3-128 C₂H₅

—

C₃H₇ 2-3-129 C₂H₅

—

C₄H₉ 2-3-130 C₂H₅

—

C₅H₁₁ 2-3-131 C₃H₇

—

CH₃ 2-3-132 C₃H₇

—

C₂H₅ 2-3-133 C₃H₇

—

C₃H₇ 2-3-134 C₃H₇

—

C₄H₉ 2-3-135 C₃H₇

—

C₅H₁₁

TABLE 148 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-136 C₄H₉

—

CH₃ 2-3-137 C₄H₉

—

C₂H₅ 2-3-138 C₄H₉

—

C₃H₇ 2-3-139 C₄H₉

—

C₄H₉ 2-3-140 C₄H₉

—

C₅H₁₁ 2-3-141 C₅H₁₁

—

CH₃ 2-3-142 C₅H₁₁

—

C₂H₅ 2-3-143 C₅H₁₁

—

C₃H₇ 2-3-144 C₅H₁₁

—

C₄H₉ 2-3-145 C₅H₁₁

—

C₅H₁₁ 2-3-146 C₂H₅O

—

C₄H₉ 2-3-147 C₅H₁₁

—

OC₂H₅ 2-3-148 C₂H₅O

—

OC₄H₉ 2-3-149 C₃H₇

—

OC₄H₉ 2-3-150 C₅H₁₁

—

OC₂H₅

TABLE 149 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-151 C₃H₇

—

C₅H₁₁ 2-3-152 C₃H₇O

—

C₅H₁₁ 2-3-153 C₅H₁₁

—

OC₂H₅ 2-3-154 CH₂═CH

—

C₅H₁₁ 2-3-155 CH₃CH═CH

—

C₂H₅ 2-3-156 CH₂═CHC₂H₄

—

C₃H₇ 2-3-157 C₃H₇CH═CH

—

CH₃ 2-3-158 CH₃CH═CHC₂H₄

—

C₂H₅ 2-3-159 C₂H₅

—

CH₂CH₂CHF₂ 2-3-160 CH₂FCH₂CH₂

—

C₄H₉ 2-3-161 CH₃

—

CH═CH₂ 2-3-162 C₄H₉

—

CH═CHCH₃ 2-3-163 C₂H₅

—

C₂H₄CH═CH₂ 2-3-164 C₃H₇

—

C₂H₄CH═CH₂ 2-3-165 C₃H₇

—

CH═CHC₃H₇

TABLE 150 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-166 C₂H₅

—

CH═CHC₃H₇ 2-3-167 C₅H₁₁

—

C₂H₄CH═CHCH₃ 2-3-168 C₃H₇

—

C₂H₄CH═CHCH₃ 2-3-169 CH₂═CH

—

C₂H₄CH═CH₂ 2-3-170 CH₃CH═CH

—

CH═CH₂ 2-3-171 C₂H₅OCH₂

—

C₃H₇ 2-3-172 C₃H₇

—

OC₂H₄CH═CH₂ 2-3-173 C₃H₇

CH₂CH₂

C₂H₅ 2-3-174 C₂H₅

C≡C

C₃H₇ 2-3-175 C₃H₇

CH₂O

C₂H₅ 2-3-176 C₂H₅

OCH₂

C₃H₇ 2-3-177 C₄H₉

COO

C₄H₉ 2-3-178 C₃H₇

OCO

H 2-3-179 C₂H₅

CF₂O

C₇H₅ 2-3-180 CH₃

OCF₂

C₂H₅

TABLE 151 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-181 CH₃

—

CH₃ 2-3-182 CH₃

—

C₂H₅ 2-3-183 CH₃

—

C₃H₇ 2-3-184 CH₃

—

C₄H₉ 2-3-185 CH₃

—

C₅H₁₁ 2-3-186 C₂H₅

—

CH₃ 2-3-187 C₂H₅

—

C₂H₅ 2-3-188 C₂H₅

—

C₃H₇ 2-3-189 C₂H₅

—

C₄H₉ 2-3-190 C₂H₅

—

C₅H₁₁ 2-3-191 C₃H₇

—

CH₃ 2-3-192 C₃H₇

—

C₂H₅ 2-3-193 C₃H₇

—

C₃H₇ 2-3-194 C₃H₇

—

C₄H₉ 2-3-195 C₃H₇

—

C₅H₁₁

TABLE 152 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-196 C₄H₉

—

CH₃ 2-3-197 C₄H₉

—

C₂H₅ 2-3-198 C₄H₉

—

C₃H₇ 2-3-199 C₄H₉

—

C₄H₉ 2-3-200 C₄H₉

—

C₅H₁₁ 2-3-201 C₅H₁₁

—

CH₃ 2-3-202 C₅H₁₁

—

C₂H₅ 2-3-203 C₅H₁₁

—

C₃H₇ 2-3-204 C₅H₁₁

—

C₄H₉ 2-3-205 C₅H₁₁

—

C₃H₇ 2-3-206 C₂H₅O

—

C₄H₉ 2-3-207 C₅H₁₁

—

OC₂H₅ 2-3-208 C₂H₅O

—

OC₄H₉ 2-3-209 C₅H₁₁

—

C₃H₇ 2-3-210 C₃H₇

—

C₅H₁₁

TABLE 153 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-211 C₂H₅

—

CH₂CH₂F 2-3-212 CH₃OC₂H₄

—

C₂H₅ 2-3-213 CH₂═CH

—

C₃H₇ 2-3-214 CH₂═CH

—

C₅H₁₁ 2-3-215 CH₃CH═CH

—

C₂H₅ 2-3-216 CH₂═CHC₂H₄

—

C₃H₇ 2-3-217 C₃H₇CH═CH

—

C₄H₉ 2-3-218 CH₃CH═CHC₂H₄

—

C₂H₅ 2-3-219 C₃H₇

—

CH═CH₂ 2-3-220 C₅H₁₁

—

CH═CH₂ 2-3-221 C₃H₇

—

CH═CHCH₃ 2-3-222 C₄H₉

—

CH═CHCH₃ 2-3-223 C₃H₇

—

C₂H₄CH═CH₂ 2-3-224 C₃H₇

—

C₂H₄CH═CH₂ 2-3-225 C₄H₉

—

CH═CHC₃H₇

TABLE 154 (2-3)

Physical property No. Ra A² A³ Z² A⁴ Rb values 2-3-226 C₂H₅

—

CH═CHC₃H₇ 2-3-227 C₂H₅

—

C₂H₄CH═CHCH₃ 2-3-228 C₃H₇

—

C₂H₄CH═CHCH₃ 2-3-229 CH₂═CH

—

CH═CH₂ 2-3-230 CH₃CH═CH

—

C₂H₄CH═CH₂ 2-3-231 CH₃OCH₂

—

C₃H₇ 2-3-232 C₂H₅

—

OC₃H₄CH═CH₂ 2-3-233 C₅H₁₁

CH₂CH₂

C₂H₅ 2-3-234 C₅H₁₁

(CH₂)₄

C₃H₇ 2-3-235 C₂H₅

CH₂O

C₃H₇ 2-3-236 C₃H₇

OCH₂

CH₃ 2-3-237 C₅H₁₁

COO

C₄H₉ 2-3-238 C₂H₅

OCO

C₃H₇ 2-3-239 C₂H₅

CF₂O

C₆H₁₃ 2-3-240 C₄H₉

OCF₂

C₂H₅

TABLE 155 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-241 CH₃

—

CH₃ 2-3-242 CH₃

—

C₂H₅ 2-3-243 CH₃

—

C₃H₇ 2-3-244 CH₃

—

C₄H₉ 2-3-245 CH₃

—

C₅H₁₁ 2-3-246 C₂H₅

—

CH₃ 2-3-247 C₂H₅

—

C₂H₅ 2-3-248 C₂H₅

—

C₃H₇ 2-3-249 C₂H₅

—

C₄H₉ 2-3-250 C₂H₅

—

C₅H₁₁ 2-3-251 C₃H₇

—

CH₃ 2-3-252 C₃H₇

—

C₂H₅ 2-3-253 C₃H₇

—

C₃H₇ 2-3-254 C₃H₇

—

C₄H₉ 2-3-255 C₃H₇

—

C₅H₁₁

TABLE 156 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-256 C₄H₉

—

CH₃ 2-3-257 C₄H₉

—

C₂H₅ 2-3-258 C₄H₉

—

C₃H₇ 2-3-259 C₄H₉

—

C₄H₉ 2-3-260 C₄H₉

—

C₅H₁₁ 2-3-261 C₅H₁₁

—

CH₃ 2-3-262 C₅H₁₁

—

C₂H₅ 2-3-263 C₅H₁₁

—

C₃H₇ 2-3-264 C₅H₁₁

—

C₄H₉ 2-3-265 C₅H₁₁

—

C₅H₁₁ 2-3-266 C₂H₅O

—

C₄H₉ 2-3-267 C₅H₁₁

—

OC₂H₅ 2-3-268 C₂H₅O

—

OC₄H₉ 2-3-269 C₃H₇

—

OC₄H₉ 2-3-270 C₅H₁₁

—

OC₂H₅

TABLE 157 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-271 C₃H₇

—

C₅H₁₁ 2-3-272 C₅H₁₁

—

C₂H₅ 2-3-273 C₄H₉O

—

C₃H₇ 2-3-274 CH₂═CH

—

C₅H₁₁ 2-3-275 CH₃CH═CH

—

C₂H₅ 2-3-276 C₃H₇CH═CH

—

C₃H₇ 2-3-277 CH₂═CHC₂H₄

—

CH₃ 2-3-278 CH₂═CHC₂H₄

—

C₂H₅ 2-3-279 CH₃CH═CHC₂H₄

—

C₃H₇ 2-3-280 CH₃CH═CHC₂H₄

—

C₄H₉ 2-3-281 C₃H₇

—

CH₂OC₃H₇ 2-3-282 C₄H₉

—

CH₂CH₂F 2-3-283 C₂H₅

—

CH═CH₂ 2-3-284 C₃H₇

—

CH═CHCH₃ 2-3-285 C₃H₇

—

CH═CHC₃H₇

TABLE 158 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-286 C₂H₅

—

C₂H₄CH═CH₂ 2-3-287 C₅H₁₁

—

C₂H₄CH═CH₂ 2-3-288 C₄H₉

—

C₂H₄CH═CHCH₃ 2-3-289 CH₂═CHC₂H₄

—

CH═CH₂ 2-3-290 CH₃CH═CHC₂H₄

—

CH═CHCH₃ 2-3-291 CH₃OCH₂CH₂

—

C₃H₇ 2-3-292 C₃H₇

—

OC₂H₄CH═CH₂ 2-3-293 C₅H₁₁

CH₂CH₂

C₂H₅ 2-3-294 C₅H₁₁

CH₂CH₂

C₃H₇ 2-3-295 C₃H₇

CH₂O

C₅H₁₁ 2-3-296 C₂H₅

OCH₂

C₃H₇ 2-3-297 C₄H₉

COO

C₄H₉ 2-3-298 C₃H₇

OCO

C₂H₅ 2-3-299 C₁₀H₂₁

CF₂O

C₂H₅ 2-3-300 CH₃

OCF₂

CH₃

TABLE 159 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-301 CH₃

—

CH₃ 2-3-302 CH₃

—

C₂H₅ 2-3-303 CH₃

—

C₃H₇ 2-3-304 CH₃

—

C₄H₉ 2-3-305 CH₃

—

C₅H₁₁ 2-3-306 C₂H₅

—

CH₃ 2-3-307 C₂H₅

—

C₂H₅ 2-3-308 C₂H₅

—

C₃H₇ 2-3-309 C₂H₅

—

C₄H₉ 2-3-310 C₂H₅

—

C₅H₁₁ 2-3-311 C₃H₇

—

CH₃ 2-3-312 C₃H₇

—

C₂H₅ 2-3-313 C₃H₇

—

C₃H₇ 2-3-314 C₃H₇

—

C₄H₉ 2-3-315 C₃H₇

—

C₅H₁₁

TABLE 160 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-316 C₄H₉

—

CH₃ 2-3-317 C₄H₉

—

C₂H₅ 2-3-318 C₄H₉

—

C₃H₇ 2-3-319 C₄H₉

—

C₄H₉ 2-3-320 C₄H₉

—

C₅H₁₁ 2-3-321 C₅H₁₁

—

CH₃ 2-3-322 C₅H₁₁

—

C₂H₅ 2-3-323 C₅H₁₁

—

C₃H₇ 2-3-324 C₅H₁₁

—

C₄H₉ 2-3-325 C₅H₁₁

—

C₅H₁₁ 2-3-326 C₂H₅O

—

C₄H₉ 2-3-327 C₅H₁₁

—

OC₂H₅ 2-3-328 C₂H₅O

—

OC₄H₉ 2-3-329 C₃H₇

—

OC₄H₉ 2-3-330 C₅H₁₁

—

OC₂H₅

TABLE 161 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-331 C₃H₇

—

C₅H₁₁ 2-3-332 C₃H₇O

—

OC₂H₅ 2-3-333 C₅H₁₁

—

OC₂H₅ 2-3-334 C₂H₅O

—

C₅H₁₁ 2-3-335 C₄H₉

—

C₂H₅ 2-3-336 C₂H₅O

—

OC₄H₉ 2-3-337 CH₂═CH

—

CH₃ 2-3-338 CH₃CH═CH

—

C₂H₅ 2-3-339 CH₂═CHC₂H₄

—

C₃H₇ 2-3-340 C₃H₇CH═CH

—

C₄H₉ 2-3-341 CH₃CH═CHC₂H₄

—

CH₃ 2-3-342 C₄H₉

—

CH═CH₂ 2-3-343 C₂H₅

—

CH═CHCH₃ 2-3-344 C₃H₇

—

CH═CHC₃H₇ 2-3-345 C₃H₇

—

C₂H₄CH═CH₂

TABLE162 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-346 C₂H₅

—

C₂H₄CH═CH₂ 2-3-347 C₅H₁₁

—

C₂H₄CH═CHCH₃ 2-3-348 C₃H₇

—

C₂H₄CH═CHCH₃ 2-3-349 CH₃CH═CHC₂H₄

—

C₂H₄CH═CH₂ 2-3-350 CH₂═CHC₂H₄

—

C₂H₄CH═CHCH₃ 2-3-351 C₄H₉OCH₂

—

C₃H₇ 2-3-352 C₃H₇

—

OC₂H₄CH═CH₂ 2-3-353 C₃H₇

CH₂CH₂

C₂H₅ 2-3-354 C₂H₅

CH₂CH₂

C₃H₇ 2-3-355 C₃H₇

CH₂O

C₂H₅ 2-3-356 C₂H₅

OCH₂

C₃H₇ 2-3-357 C₄H₉O

COO

C₄H₉ 2-3-358 C₃H₇

OCO

C₇H₁₅ 2-3-359 C₂H₅

CF₂O

C₄H₉ 2-3-360 CH₃

OCF₂

C₂H₅

TABLE 163 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-361 C₃H₇

—

C₅H₁₁ 2-3-362 C₅H₁₁

—

C₂H₅ 2-3-363 CH₃

—

C₃H₇ 2-3-364 C₄H₉

—

C₂H₅ 2-3-365 C₅H₁₁

—

OC₄H₉ 2-3-366 CH₃

—

C₂H₅ 2-3-367 C₂H₅

—

C₃H₇ 2-3-368 C₂H₅

—

C₃H₇ 2-3-369 C₃H₇O

—

C₄H₉ 2-3-370 C₂H₅

—

C₅H₁₁ 2-3-371 C₃H₇

—

C₄H₉ 2-3-372 C₃H₇

—

C₂H₅ 2-3-373 C₂H₅

—

C₅H₁₁ 2-3-374 C₃H₇

—

C₄H₉ 2-3-375 C₃H₇

—

C₅H₁₁

TABLE 164 (2-3)

No. Ra A² A³ Z² A⁴ Rb Physical property values 2-3-376 C₄H₉

—

C₅H₁₁ 2-3-377 C₅H₁₁

—

C₂H₅ 2-3-378 C₄H₉

—

C₃H₇ 2-3-379 C₄H₉

—

C₄H₉ 2-3-380 C₄H₉

—

C₅H₁₁ 2-3-381 C₅H₁₁

—

OC₄H₉ 2-3-382 C₅H₁₁

—

C₂H₅ 2-3-383 C₅H₁₁

—

C₃H₇ 2-3-384 C₅H₁₁

—

C₄H₉ 2-3-385 CH₃O

—

C₅H₁₁ 2-3-386 C₂H₅O

—

C₄H₉ 2-3-387 C₅H₁₁

—

CH₃ 2-3-388 C₄H₉O

—

C₅H₁₁ 2-3-389 C₅H₁₁

—

C₃H₇ 2-3-390 C₃H₇

—

C₅H₁₁

Comparative Example 1

As a comparative example,2,3-difluoro-4-(trans-4-pentylcyclohexylmethoxy)-4′-propylbiphenyl(R-1), which had three rings and a methyleneoxy bonding group, wassynthesized.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified as2,3-difluoro-4-(trans-4-pentylcyclohexylmethoxy)-4′-propylbiphenyl(R-1). The measurement solvent was CDCl₃.

Chemical shift δ (ppm); 7.42(d, 2H), 7.24(d, 2H), 7.07(t, 1H), 6.77(t,1H), 3.86(d, 2H), 2.63(t, 2H), 1.97-1.89(m, 2H), 1.87-1.76(m, 3H),1.68(sext, 2H), 1.36-1.17(m, 9H), 1.13-1.02(m, 2H), and 1.01-0.86(m,8H).

The phase transition temperature of the compound (R-1) obtained was asfollows.

Phase transition temperature: C 50.4 N 116.8 Iso.

A liquid crystal composition A consisting of 85% by weight of the motherliquid crystals (i) and 15% by weight of the compound (R-1) wasprepared. The physical property-values of the liquid crystal compositionobtained were measured, and the extrapolated values of the physicalproperties of the liquid crystal compound (R-1) were calculated byextrapolating the measured values. The values were as follows.

Maximum temperature (T_(NI))=115.3° C.; dielectric anisotropy Δε=−6.05;optical anisotropy (Δn)=0.155; viscosity (η)=61.2 mPa·s

Physical properties of liquid crystal compound (No. 1-1-203):

Five compounds for the mother liquid crystals (i) described above weremixed to prepare the mother liquid crystals (i) having a nematic phase.The physical properties of the mother liquid crystals (i) were asfollows.

Maximum temperature (T_(NI))=71.7° C.; optical anisotropy (Δn)=0.137;dielectric anisotropy (Δε)=11.0.

The physical property-values of the liquid crystal composition composedof 85% by weight of the mother liquid crystals (i) and 15% by weight of2,3-difluoro-4-(trans-4′-pentylbicyclohexyl-trans-4-ylmethoxy)-4′-biphenyl(No. 1-1-203) obtained in Example 7, as described above, were asfollows.

Maximum temperature (T_(NI))=214.6° C.; dielectric anisotropy (Δε)=−4.7;optical anisotropy (Δn)=0.167; viscosity (η)=53.7 mPa·s.

From these results it was found that the liquid crystal compound (No.1-1-203) had a high maximum temperature (T_(NI)), a large negativedielectric anisotropy (Δε), and a low viscosity (η).

The compound (No. 1-1-203) of the invention was found to be excellent inview of wide liquid crystal phases, a high maximum temperature (T_(NI))of a nematic phase, and a low viscosity (η) in comparison with thiscompound (R-1).

Comparative Example 2

As a comparative example, trans-4′-pentylbicyclohexyl-trans-4-carboxylicacid 4-(trans-4-propylcyclohexyl)phenylester (R-2), which had four ringsand an ester bonding group, was synthesized.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified astrans-4′-pentylbicyclohexyl-trans-4-carboxylic acid4-(trans-4-propylcyclohexyl) phenylester (R-2). The measurement solventwas CDCl₃.

Chemical shift δ (ppm) ; 7.18(d, 2H), 6.95(d, 2H) and 2.44(m, 2H),2.17-2.11(m, 2H), 1.90-1.81(m, 6H), 1.80-1.67(m, 4H), and 1.57-0.80(m,34H).

The phase transition temperature of the compound (R-1) obtained was asfollows.

Phase transition temperature: Cr 34.1 SmB 227.5 N 303.0 Iso.

The liquid crystal composition C composed of 85% by weight of motherliquid crystals (i) and 15% by weight of the compound (R-1) obtained wasprepared. The dielectric anisotropy (Δε) of the liquid crystalcomposition C obtained was measured, and the extrapolated value ofdielectric anisotropy (Δε) of the liquid crystal compound (R-2) wascalculated by extrapolating the measured values. The value was asfollows.

Dielectric anisotropy (Δε)=−0.49.

Physical properties of liquid crystal compound (No. 1-2-23):

The physical property-values of the liquid crystal composition composedof 85% by weight of the mother liquid crystals (i) and 15% by weight oftrans-4′-pentylbicyclohexyl-trans-4-carboxylic acid2,3-difluoro-4-(trans-4-propylcyclohexyl)phenylester (No. 1-2-23)obtained in Example 11, as described above, was as follows.

Maximum temperature (T_(NI))=255.9° C.; dielectric anisotropy (Δε)=−3.6;optical anisotropy (Δn)=0.114.

These values show that the liquid crystal compound (No. 1-2-23) has ahigh maximum temperature (T_(NI)) and a large negative dielectricanisotropy (Δε).

Comparison of this compound (R-2) with the compound (No. 1-2-23) of theinvention showed that the compound (No. 1-2-23) of the invention isexcellent in having a large negative dielectric anisotropy.

Comparative Example 3

As a comparative example,trans-4-{difluoro-[4-(trans-methylcyclohexyl)phenoxy]methyl}-trans-4′-pentylbicyclohexyl(R-3), which had four rings and a difluoromethyleneoxy bonding group,and was described in patent document No. 5 (DE 10,136,751), wassynthesized.

Chemical shifts δ (ppm) in ¹H-NMR analysis were described below, and thecompound obtained was identified astrans-4-{difluoro-[4-(trans-methylcyclohexyl)phenoxy]methyl}-trans-4′-pentylbicyclohexyl(R-3). The measurement solvent was CDCl₃.

Chemical shift δ (ppm); 7.14(d, 2H), 7.06(d, 2H) and 2.43(tt, 1H),2.08-1.92(m, 3H), 1.89-1.67(m, 10H), and 1.48-0.79(m, 30H).

The phase transition temperature of the compound (R-3) obtained was asfollows.

Phase transition temperature: Cr 51.5 SmB 190.7 N 255.5 Iso.Furthermore, the liquid crystal composition E composed of 85% by weightof the mother liquid crystals (i) and 15% by weight of the compound(R-3) was prepared. The dielectric anisotropy (Δε) of the liquid crystalcomposition E obtained was measured, and the extrapolated value of thedielectric anisotropy (Δε) of the liquid crystal compound (R-1) wascalculated by extrapolating the measured values. The value was asfollows.

Dielectric anisotropy (Δε)=+0.18.

Physical Properties of Liquid Crystal Compound (No. 1-3-203):

The physical-property values of the liquid crystal composition composedof 85% by weight of the mother liquid crystal (i) and 15% by weight of4-[difluoro-(trans-4′-pentylbicyclohexyl-3-ene-4-yl)methoxy]-2,3-difluoro-4′-propylbiphenyl (No. 1-3-203) obtained inExample 14, as described above, were as follows.

Maximum temperature (T_(NI))=219.9° C.; dielectric anisotropy(Δε)=−1.55; optical anisotropy (Δn)=0.140; viscosity (n); 43.7 mPa·s.

From these results it was found the liquid crystal compound (No.1-3-203) had a high maximum temperature (T_(NI)) and a large negativedielectric anisotropy (Δε).

The compound (No. 1-3-203) of the invention was found to be excellent inview of a wide nematic phase and a large negative dielectric anisotropy(Δε) in comparison with this compound (R-3).

Example 17 Examples of Liquid Crystal Compositions

The representative compositions of the invention are summarized inComposition Example 1 to Composition Example 12. First, compounds whichare the components of a composition, and its amount (% by weight) areshown. The compounds are indicated, according to the definition in Table165, with the symbols of the left-terminal group, bonding group, ringstructure, and right-terminal group. The configuration of1,4-cyclohexylene is a trans form. When the sign of the terminal groupis absent, the terminal group means hydrogen. Next, the physicalproperty-values of the composition are shown. The physicalproperty-values here are measured values themselves.

TABLE 165 Method of Description of Compound using Symbols

1) Left-Terminal Group R— Symbol C_(n)H_(2n+1)  n  C_(n)H_(2n+1)O  nO C_(m)H_(2m+1)OC_(n)H_(2n) mOn  CH₂═CH  V  C_(n)H_(2n+1) CH═CH  nV CH₂═CH C_(n)H_(2n)  Vn  C_(m)H_(2m+1) CH═CH C_(n)H_(2n)  mVN  CF₂═CH VFF  CF₂═CH C_(n)H_(2n)  VFFn  2) Right-Terminal Group  R′ Symbol C_(n)H_(2n+1)  n  OC_(n)H_(2n+1)  On  CH═CH₂  V  CH═CH C_(n)H_(2n+1) Vn  C_(n)H_(2n) CH═CH₂  nV  CH═CF₂  VFF  COOCH₃  EMe 3) Bonding Group Z_(n)   Symbol  CnH_(2n)  n  COO  E  CH═CH  V  CH₂O  1O  OCH₂  O1 CF₂O  X 4) Ring Structure  A_(n)  Symbol

H

Ch

B

B(2F)

B(3F)

B(2F,3F)

B(2F,3Cl)

B(2Cl,3F) 5) Example of Description Example 1. 5-HH1OB(2F,3F)H-3

Example 2. 5-HHEB(2F,3F)H-3

Example 3. 5-HBB(3F)B-3

Example 4. 5-HBB(2F,3F)-O2

Physical property-values were measured according to the followingmethods. Many of these measurement methods were described in theStandard of Electric Industries Association of Japan, EIAJ-ED-2521A, orthose with some modifications.

(1) Maximum Temperature of Nematic Phase (NI; ° C.)

A sample was put on a hot plate in a melting point apparatus equippedwith a polarizing microscope, and heated at the rate of 1° C. perminute. A temperature was measured when part of sample changed from anematic phase to an isotropic liquid. Hereinafter, the maximumtemperature of a nematic phase may be abbreviated to “maximumtemperature.”

(2) Minimum Temperature of Nematic Phase (TC; ° C.)

Samples having a nematic phase were respectively kept in freezers at 0°C., −10° C., −20° C., −30° C., and −40° C. for ten days, and then liquidcrystal phases were observed. For example, when a sample still remainedin a nematic phase at −20° C., and changed to crystals (or a smecticphase) at −30° C., T_(c) was expressed as −20° C. Hereinafter, theminimum temperature of a nematic phase may be abbreviated to “minimumtemperature.”

(3) Optical anisotropy (Δn; measured at 25° C.)

The optical anisotropy was measured by use of an Abbe refractometer witha polarizing plate attached to the ocular, using light at a wavelengthof 589 nm. The surface of a main prism was rubbed in one direction, andthen a sample was dropped onto the main prism. A refractive index (n∥)was measured when the direction of polarization was parallel to that ofrubbing and a refractive index (n⊥) was measured when the direction ofpolarization was perpendicular to that of rubbing. The value (Δn) ofoptical anisotropy was calculated from the formula of Δn=n∥−n⊥.

(4) Viscosity (Δε; measured at 20° C.; mPa·s)

An E type viscometer was used for measurement.

(5) Dielectric Anisotropy (Δε; measured at 25° C.)

An ethanol (20 mL) solution of octadecyltriethoxysilane (0.16 mL) wasapplied to well-washed glass substrates. The glass substrates wererotated with a spinner, and then heated at 150° C. for 1 hour. A VAdevice in which a distance (cell gap) was 20 μm was assembled from thetwo glass substrates. A polyimide alignment film was prepared on glasssubstrates in a similar manner. After a rubbing-treatment to thealignment film obtained on the glass substrates, a TN device in which adistance between the two glass substrates was 9 μm and the twist anglewas 80 degrees was assembled.

A sample (a liquid crystal composition, or a mixture of a liquid crystalcompound and mother liquid crystals) was put in the VA device obtained,applied with a voltage of 0.5 V (1 kHz, sine waves), and then adielectric constant (ε∥) in a major axis direction of the liquid crystalmolecules was measured. The sample (the liquid crystal composition, orthe mixture of the liquid crystal compound and the mother liquidcrystals) was put in the TN device obtained, applied with a voltage of0.5 V (1 kHz, sine waves), and then the dielectric constant (ε⊥) in aminor axis direction of liquid crystal molecules was measured. The valueof dielectric anisotropy was calculated from the equation of Δε=ε∥−ε⊥. Acomposition in which this value is negative has a negative dielectricanisotropy.

(6) Voltage Holding Ratio (VHR; measured at 25° C. and 100° C.; %)

A TN device was prepared by putting a sample in a cell which has apolyimide alignment film and a distance between two glass substrates(cell gap) of 6 μm. The TN device was charged at 25° C. by applyingpulse voltage (60 microseconds at 5V). The waveforms of the voltageapplied to the TN device were observed with a cathode ray oscilloscopeand an area between a voltage curve and a horizontal axis in a unitperiod (16.7 milliseconds) was measured. An area was similarly measuredbased on the waveform of the applied voltage after the TN device hadbeen removed. The value of the voltage holding ratio (%) was calculatedfrom the equation: (voltage holding ratio)=(value of the area in thepresence of a TN device)/(value of the area in the absence of TNdevice)×100.

The ratio (percentage) of components or liquid crystal compounds is theweight percentage (% by weight) based on the total weight of the liquidcrystal compound. A composition is prepared by mixing components, suchas liquid crystal compounds, after the weight of the components has beenmeasured. Therefore, it is easy to calculate the % by weight of thecomponents.

Composition Example 1

V-H1OB(2F,3F)HH-3  5% 5-H1OB(2F,3F)HH-3  5% 2-HH-3  8% 3-H2H—V  5%3-HB—O2 12% 5-HB—O2 13% 3-HHB-1  7% V2—HHB-1 10% 3-H2B(2F,3F)—O2 12%5-H2B(2F,3F)—O2 13% 3-HBB(2F,3F)—O2  5% 5-HBB(2F,3F)—O2  5% NI = 82.3°C.; Δn = 0.093; Δε = −2.5.

Composition Example 2

5-H1OB(2F,3F)HH-3  5% 3-HH1OB(2F,3F)B(3F)—O4  5% 2-HH-3  5% 2-H2H-3  5%3-HB—O2 16% 5-HB—O2 16% V—HHB-1 11% 3-H2B(2F,3F)—O2 13% 5-H2B(2F,3F)—O214% 3-HBB(2F,3F)—O2  5% 5-HBB(2F,3F)—O2  5% NI = 71.0° C.; Δn = 0.097;Δε = −2.9.

Composition Example 3

V—H1OB(2F,3F)HH-3  3% 5-H1OB(2F,3F)HH-3  5% 5-H1OB(2F,3F)BH-3  5%5-H1OB(2F,3F)BB-3  3% 2-H2H-3 10% 3-H2H—V 15% 3-HB—O2 11% 5-HB—O2 11%3-H2B(2F,3F)—O2 17% 3-HBB(2F,3F)—O2 10% 5-HBB(2F,3F)—O2 10% NI = 82.0°C.; TC =< −20° C.; Δn = 0.100; Δε = −3.4.

Composition Example 4

5-HH1OB(2F,3F)H-3  6% 5-HH1OB(2F,3F)B-3  5% 3-H2H—V 17% 3-HB—O2  7%3-HHB-1  5% V2—HHB-1  3% 3-HHB—O1  5% 3-H2B(2F,3F)—O2 18%5-H2B(2F,3F)—O2 19% 3-HBB(2F,3F)—O2  7% 5-HBB(2F,3F)—O2  8% NI = 81.4°C.; TC =< −20° C.; Δn = 0.096; Δε = −3.4.

Composition Example 5

5-HHEB(2F,3F)H-3  5% 5-HBEB(2F,3F)H-3  3% 5-HB(3F)EB(2F,3F)H-3  3%2-H2H-3  5% 3-H2H—V 17% V—HHB-1  8% 3-HBB-2  5% 3-HB(2F,3F)—O2 10%3-H2B(2F,3F)—O2 20% 3-HBB(2F,3F)—O2  8% 5-HBB(2F,3F)—O2 10%3-HBB(2F,3Cl)—O2  3% 3-HBB(2Cl,3F)—O2  3% NI = 87.7° C.; TC <= −20° C.;Δn = 0.103; Δε = −3.4.

Composition Example 6

5-BBEB(2F,3F)H-3  5% 5-HHEB(2F,3F)B-3  8% 5-HBEB(2F,3F)B-3  3% 2-H2H-3 5% 3-H2H—V  6% 3-HB—O2 18% 5-HB(2F,3F)—O2 10% 3-H2B(2F,3F)—O2 20%2-HHB(2F,3F)-1  5% 3-HHB(2F,3F)—O2 10% 5-HHB(2F,3F)—O2 10% NI = 85.7°C.; TC <= −20° C.; Δn = 0.098; Δε = −3.5.

Composition Example 7

5-BBEB(2F,3F)B-3  5% 5-HEB(2F,3F)HH-3  5% 5-BEB(2F,3F)HH-3  5% 2-H2H-315% 3-H2H—V  5% 3-HHB-3  5% 2-BBB(2F)-3  5% 3-H2B(2F,3F)—O2 20%5-H2B(2F,3F)—O2 15% 3-HH2B(2F,3F)—O2 10% 5-HH2B(2F,3F)—O2 10% NI = 84.9°C.; TC <= −20° C.; Δn = 0.096; Δε = −3.5.

Composition Example 8

5-HChXB (2F,3F) B-3 5% 5-HHXB (2F,3F) B-3 5% 2-H2H-3 6% 3-H2H—V 17%3-HHEH-3 3% 3-HHEH-5 3% 3-HB (2F,3F) —O2 11% 5-HB (2F,3F) —O2 11% 5-HB(2F,3Cl) —O2 5% 3-HB (2Cl,3F) —O2 5% 5-HHB (2F,3F) —O2 5% 3-HH2B (2F,3F)—O2 12% 5-HH2B (2F,3F) —O2 12% NI = 81.6° C.; Δn = 0.077; Δε = −3.4.

Composition Example 9

3-HH1OB(2F,3F)B(3F)—O4  5% 3-HHEB(2F,3F)B(3F)—O4  5% 3-HB—O2 16% V—HHB-118% 3-H2B(2F,3F)—O2 20% 5-H2B(2F,3F)—O2 20% 3-HH2B(2F,3F)—O2  8%5-HH2B(2F,3F)—O2  8% NI = 82.5° C.; TC <= −20° C.; Δn = 0.100; Δε =−3.5.

Composition Example 10

V—HH1OB(2F,3F)B-3  8% V—HH1OB(2F,3F)H-3  7% 2-H2H-3  5% 3-H2H—V 17%3-HBBH-5  3% 1O1—HBBH-4  3% 5-HBB(3F)B-2  3% V—HB(2F,3F)—O2  7%5-HB(2F,3F)—O2  7% 3-H2B(2F,3F)—O2 12% 5-H2B(2F,3F)—O2 12%3-HBB(2F,3F)—O2  8% 5-HBB(2F,3F)—O2  8% NI = 80.7° C.; TC <= −20° C.; Δn= 0.099; Δε = −3.4.NI=87.2° C.; TC<=−20° C.; Δn=0.097; Δε=−3.4.

Composition Example 11

5-HHEB(2F,3F)H-3  6% 5-HEB(2F,3F)HH-3  5% 2-H2H-3 10% 3-H2H—V 15%2-BB(3F)B-3  5% 5-HBB(3F)B-2  5% 3-H2B(2F,3F)—O2 16% 5-H2B(2F,3F)—O2 16%V—HHB(2F,3F)—O2  5% 5-HHB(2F,3F)—O2  6% 5-HBB(2F,3F)—O2  5%3-HHB(2F,3Cl)—O2  3% 3-HHB(2Cl,3F)—O2  3% NI = 87.3° C.; TC <= −20° C.;Δn = 0.097; Δε = −3.4.

Comparative Composition Example 1

Comparative Composition Example 1 containing the compound (R-1) obtainedin Comparative Example 1 and a compound similar to the compound (R-1)was prepared in order to compare with Composition Example 1.

The characteristics were as follows.

5-H1OB(2F,3F)B-3 (R-1)  5% 5-H1OB(2F,3F)B—O2  5% 2-HH-3  8% 3-H2H—V  5%3-HB—O2 12% 5-HB—O2 13% 3-HHB-1  7% V2—HHB -1 10% 3-H2B(2F,3F)—O2 12%5-H2B(2F,3F)—O2 13% 3-HBB(2F,3F)—O2  5% 5-HBB(2F,3F)—O2  5% NI = 71.5°C.; Δn = 0.097; Δε = −2.5.

NI=71.5° C.; Δn=0.097; Δε=−2.5.

The composition in Composition Example 1 was found to have a highermaximum temperature (NI) of a nematic phase in comparison with thecomposition in Comparative Composition Example 1.

Comparative Composition Example 2

Comparative Composition Example 2, in which the compound (R-2) obtainedin Comparative Example 2 and a compound similar to the compound (R-2)were contained, was prepared in order to compare with CompositionExample 2. The characteristics were as follows.

3-HHEBH-3 5% 5-HHEBH-3 (R-2) 5% 2-HH-3 5% 2-H2H-3 5% 3-HB—O2 16% 5-HB—O216% V—HHB-1 11% 3-H2B (2F,3F) —O2 13% 5-H2B (2F,3F) —O2 14% 3-HBB(2F,3F) —O2 5% 5-HBB (2F,3F) —O2 5% Δn = 0.092; Δε = −2.3.

Δn=0.092; Δε=−2.3.

The composition in Composition Example 2 was found to have a largernegative dielectric anisotropy (Δε) in comparison with the compositionin Comparative Composition Example 2.

INDUSTRIAL APPLICABILITY

The liquid crystal compound of the invention can be used as a materialfor a liquid crystal display device, and a liquid crystal compositionincluding this compound can be suitably used for a liquid crystaldisplay device.

1. A compound represented by formula (a):

wherein a and Rb are each independently hydrogen, alkyl having 1 to 12carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons,alkoxyalkyl having 2 to 11 carbons, or alkenyloxy having 2 to 11carbons, and in these alkyl, alkenyl, alkoxy, alkoxyalkyl, andalkenyloxy, arbitrary hydrogen may be replaced by fluorine; ring A¹,ring A², ring A³, and ring A⁴ are each independently 1,4-cyclohexylene,1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene,2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, naphthalene-2,6-diyl,decahydronaphthalene-2,6-diyl, or1,2,3,4-tetrahydronaphthalene-2,6-diyl; Z¹ and Z² are each independentlya single bond, —(CH₂)₂—, —(CH₂)₄—, —CH═CH—, —C≡C—, —CH₂O—, —OCH₂—,—COO—, —OCO—, —CF₂O—, or —OCF₂—; W is —CH₂—, —CO—, or —CF₂—; and m and nare each independently 0, 1, or 2, and the sum of m and n is 1 or 2,provided that when m=1 and n=0, ring A³ is 1,4-cyclohexylene; when ringA² is 3-fluoro-1,4-phenylene, W is —CH₂— or —CF₂—.
 2. The compoundaccording to claim 1, wherein Ra and Rb are each independently alkylhaving 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1to 11 carbons, alkoxyalkyl having 2 to 11 carbons, or alkenyloxy having2 to 11 carbons; and ring A¹, ring A², ring A³, and ring A⁴ are eachindependently 1,4-cyclohexylene, 1,4-cyclohexenylene,tetrahydropyran-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, or3-fluoro-1,4-phenylene.
 3. A compound represented by any one of formula(a-1) and formula (a-2):

wherein Ra¹ and Rb¹ are each independently alkyl having 1 to 12 carbons,alkoxy having 1 to 11 carbons, or alkenyl having 2 to 12 carbons; ringA⁵, ring A⁶, ring A⁷, and ring A⁸ are each independently1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or3-fluoro-1,4-phenylene; Z³ and Z⁴ are each independently a single bondor —(CH₂)₂—,; and W is —CH₂—, —CO—, or —CF₂—; provided that when ring A⁶is 3-fluoro-1,4-phenylene, W is —CH₂— or —CF₂—.
 4. (canceled)
 5. Acompound represented by any one of formulas (a-1-1) to (a-1-3) andformulas (a-2-1) to (a-2-6):

wherein Ra¹ and Rb¹ are each independently alkyl having 1 to 12 carbons,alkoxy having 1 to 11 carbons, or alkenyl having 2 to 12 carbons; and Wis —CH₂—, —CO—, or —CF₂—.
 6. The compound according to claim 5, whereinW is —CH₂— in formulas (a-1-1) to (a-1-3) and formulas (a-2-1) to(a-2-6).
 7. The compound according to claim 5, wherein W is —CO— informulas (a-1-1) to (a-1-3) and formulas (a-2-1) to (a-2-6).
 8. Thecompound according to claim 5, wherein W is —CF₂— in formulas (a-1-1) to(a-1-3) and formulas (a-2-1) to (a-2-6).
 9. A liquid crystal compositionhaving a negative dielectric anisotropy that comprises a first componentwhich is at least one compound selected from the group of compoundsaccording to claim 1 and a second component which is at least onecompound selected from the group of compounds represented by formulas(e-1) to (e-3):

wherein Ra₁₁ and Rb₁₁ are each independently alkyl having 1 to 10carbons, and in this alkyl, —CH₂— may be nonadjacently replaced by —O—,—(CH₂)₂— may be nonadjacently replaced by —CH═CH—, and hydrogen may bereplaced by fluorine; ring A¹¹, ring A¹², ring A¹³, and ring A¹⁴ areeach independently 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, pyrimidine-2,5-diyl,1,3-dioxane-2,5-diyl, or tetrahydropyran-2,5-diyl; and Z¹¹, Z¹², and Z¹³are each independently a single bond, —(CH₂)₂—, —CH═CH—, —C≡C—, —COO—,or —CH₂O—.
 10. A liquid crystal composition having a negative dielectricanisotropy that comprises a first component which is at least onecompound selected from the group of compounds represented by formulas(a-1-1) to (a-1-3) and formulas (a-2-1) to (a-2-6) according to claim 5,and a second component selected from the group of compounds representedby formulas (e-1) to (e-3) according to claim
 9. 11. The liquid crystalcomposition according to claim 10, wherein the content ratio of thefirst component is in the range of 5% to 60% by weight, and the contentratio of the second component is in the range of 40% to 95% by weight,based on the total weight of the liquid crystal composition.
 12. Theliquid crystal composition according to claim 11 that further comprisesa third component which is at least one compound selected from the groupof compounds represented by formulas (g-1) to (g-6), in addition to thefirst and second components:

wherein Ra₂₁ and Rb₂₁ are each independently hydrogen or alkyl having 1to 10 carbons, and in this alkyl, —CH₂— may be nonadjacently replaced by—O—, —(CH₂)₂— may be nonadjacently replaced by —CH═CH—, and hydrogen maybe replaced by fluorine; ring A²¹, ring A²², and ring A²³ are eachindependently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,3-fluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3 -dioxane-2,5-diyl, ortetrahydropyran-2,5-diyl; Z²¹, Z²², and Z²³ are each independently asingle bond, —(CH₂)₂—, —CH═CH—, —C≡C—, —OCF₂—, —CF₂O—, —OCF₂CH₂CH₂—,—CH₂CH₂CF₂O—, —COO—, —OCO—, —OCH₂—, or —CH₂O—; Y¹, Y², and Y⁴ are eachindependently fluorine or chlorine; q, r, and s are each independently0, 1, or 2, and q+r+s is 1, 2, or 3; and t is 0, 1, or
 2. 13. The liquidcrystal composition according to claim 12, wherein the third componentis at least one compound selected from the group of compoundsrepresented by formulas (h-1) to (h-7):

wherein Ra₂₂ and Rb₂₂ are a straight-chain alkyl having 1 to 8 carbons,a straight-chain alkenyl having 2 to 8 carbons, or alkoxy having 1 to 7carbons; Z²⁴, Z²⁵, and Z²⁶ are a single bond, —(CH₂)₂—, —COO—, —OCO—,—CH₂O—, or —OCH₂—; and Y¹ and Y² are simultaneously fluorine or one ofY¹ and Y² is fluorine and the other is chlorine.
 14. A liquid crystalcomposition having a negative dielectric anisotropy that comprises afirst component which is at least one compound selected from the groupof compounds represented by formulas (a-1-1) to (a-1-3) and formulas(a-2-1) to (a-2-6) according to claim 5, a second component which is atleast one compound selected from the group of compounds represented byformulas (e-1) to (e-3) according to claim 9, and a third componentwhich is at least one compound selected from the group of compoundsrepresented by formulas (h-1) to (h-7) according to claim
 13. 15. Theliquid crystal composition according to claim 14, wherein the contentratio of the first component is in the range of 5% to 60% by weight, thecontent ratio of the second component is in the range of 20% to 75% byweight, and the content ratio of the third component is in the range of20% to 75% by weight, based on the total weight of the liquid crystalcomposition.
 16. A liquid crystal display device that comprises theliquid crystal composition according to claim
 9. 17. The liquid crystaldisplay device according to claim 16, wherein the operation mode thereofis a VA mode or an IPS mode, and the driving mode thereof is an activematrix mode.
 18. A liquid crystal composition having a negativedielectric anisotropy that comprises a first component which is at leastone compound selected from the group of compounds represented byformulas (a-1) and (a-2) according to claim 3 and a second componentwhich is at least one compound selected from the group of compoundsrepresented by formulas (e-1) to (e-3) according to claim
 9. 19. Aliquid crystal display device that comprises the liquid crystalcomposition according to claim
 13. 20. The liquid crystal display deviceaccording to claim 19, wherein the operation mode thereof is a VA modeor an IPS mode, and the driving mode thereof is an active matrix mode.